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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1205–o1206.
Published online 2010 April 28. doi:  10.1107/S1600536810015023
PMCID: PMC2979269

4-[6,8-Dibromo-2-(2-chloro-5-nitro­phen­yl)-1,2,3,4-tetra­hydro­quinazolin-3-yl]cyclo­hexa­nol

Abstract

The title compound, C20H20Br2ClN3O3, was synthesized by the condensation reaction of 2-chloro-5-nitro­benzaldehyde with 4-(2-amino-3,5-dibromo­benzyl­amino)cyclo­hexa­nol in a methanol solution. There are two independent mol­ecules in the asymmetric unit and in one mol­ecule the atoms of the cyclo­hexane ring are disordered over two sets of sites with refined occupancies of 0.657 (12) and 0.343 (12). The dihedral angle between the two benzene rings is 89.5 (2)° in one mol­ecule and 82.9 (2)° in the other. In the crystal structure, inter­molecular N—H(...)O and O—H(...)O hydrogen bonds link the mol­ecules into chains propagating along [01An external file that holds a picture, illustration, etc.
Object name is e-66-o1205-efi1.jpg].

Related literature

For details of the pharmaceutical uses of Ambroxol, systematic name 4-(2-amino-3,5-dibromo­benzyl­amino)cyclo­hexa­nol, a compound closely related to the title compound see: Felix et al. (2008 [triangle]); Gaida et al. (2005 [triangle]); Lee et al. (2004 [triangle]). For a related structure, see: Wang et al. (2009 [triangle]). For standard bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1205-scheme1.jpg

Experimental

Crystal data

  • C20H20Br2ClN3O3
  • M r = 545.66
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1205-efi2.jpg
  • a = 10.2614 (13) Å
  • b = 13.1418 (17) Å
  • c = 16.931 (2) Å
  • α = 83.764 (2)°
  • β = 73.309 (2)°
  • γ = 84.750 (2)°
  • V = 2169.8 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.89 mm−1
  • T = 298 K
  • 0.30 × 0.28 × 0.28 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.389, T max = 0.409
  • 11972 measured reflections
  • 8470 independent reflections
  • 4874 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.154
  • S = 1.02
  • 8470 reflections
  • 578 parameters
  • 122 restraints
  • H-atom parameters constrained
  • Δρmax = 1.56 e Å−3
  • Δρmin = −1.07 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015023/lh5014sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015023/lh5014Isup2.hkl

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

Acknowledgments

Financial support from the Third Affiliated Hospital of Soochow University is acknowledged.

supplementary crystallographic information

Comment

Ambroxol, 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol, is an expectorant agent which leads to bronchial secretion due to its mucolytic properties (Felix et al., 2008; Gaida et al., 2005; Lee et al., 2004). Recently, we reported the crystal structure of a derivative of Ambroxol (Wang et al., 2009). In this paper, the crystal structure of the title compound, derived from the condensation reaction of 2-chloro-5-nitrobenzaldehyde with 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol in methanol solution, is reported.

There are two independent molecules in the asymmetric unit of the title compound, Fig. 1. The dihedral angle between the two benzene rings is 89.5 (2)° in one molecule and 82.9 (2)° in the other. The cyclohexyl rings adopt chair configurations. All bond lengths are within normal ranges (Allen et al., 1987).

Experimental

2-Chloro-5-nitrobenzaldehyde (1.0 mol, 185.6 mg) and 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol (1.0 mmol, 378.1 mg) were dissolved in a methanol solution (30 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent for a week at room temperature.

Refinement

H atoms were included in calulated positions with, with C–H = 0.93–0.98 Å, N-H = 0.86Å and O-H = 0.84 with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O). The C29-C34 cyclohexyl ring is disordered over two distinct sites, with refined occupancies of 0.657 (12) and 0.343 (12). Bond length restraints were applied to the disorder model using the SADI commmand in SHELXL (Sheldrick, 2008).

Figures

Fig. 1.
The asymmetric unit of the title compound showing 30% probability ellipsoids. H atoms bonded to C atoms are not shown.

Crystal data

C20H20Br2ClN3O3Z = 4
Mr = 545.66F(000) = 1088
Triclinic, P1Dx = 1.670 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2614 (13) ÅCell parameters from 2646 reflections
b = 13.1418 (17) Åθ = 2.5–24.5°
c = 16.931 (2) ŵ = 3.89 mm1
α = 83.764 (2)°T = 298 K
β = 73.309 (2)°Block, colorless
γ = 84.750 (2)°0.30 × 0.28 × 0.28 mm
V = 2169.8 (5) Å3

Data collection

Bruker SMART CCD area-detector diffractometer8470 independent reflections
Radiation source: fine-focus sealed tube4874 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 26.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→7
Tmin = 0.389, Tmax = 0.409k = −15→16
11972 measured reflectionsl = −21→20

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0631P)2 + 2.7275P] where P = (Fo2 + 2Fc2)/3
8470 reflections(Δ/σ)max = 0.001
578 parametersΔρmax = 1.56 e Å3
122 restraintsΔρmin = −1.06 e Å3

Special details

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*/UeqOcc. (<1)
Br10.39058 (9)−0.05133 (6)0.42693 (4)0.0888 (3)
Br2−0.06018 (7)0.08773 (7)0.30819 (7)0.1156 (4)
Br30.65212 (7)0.61194 (6)0.35191 (6)0.0919 (3)
Br40.59092 (6)0.18627 (5)0.36046 (5)0.0747 (2)
Cl10.87128 (15)−0.09542 (13)0.01005 (10)0.0700 (4)
Cl2−0.17164 (14)0.27481 (12)0.47738 (9)0.0628 (4)
O10.4691 (6)−0.4725 (4)0.1616 (4)0.133 (3)
O20.3509 (5)−0.3554 (4)0.2309 (4)0.0953 (16)
O30.8184 (5)0.4244 (3)0.0419 (3)0.0816 (14)
H30.85610.4573−0.00300.122*
O40.2375 (7)0.1609 (5)0.7120 (4)0.119 (2)
O50.0491 (7)0.1570 (6)0.8042 (4)0.145 (3)
N10.4516 (6)−0.3856 (4)0.1802 (4)0.0731 (15)
N20.5854 (4)0.0384 (3)0.0978 (3)0.0435 (10)
N30.5434 (4)−0.0321 (3)0.2395 (2)0.0472 (11)
H3N0.5793−0.04640.27970.057*
N40.1168 (8)0.1719 (5)0.7331 (4)0.0849 (18)
N50.1019 (4)0.3814 (3)0.4122 (2)0.0425 (10)
N60.2870 (4)0.2572 (3)0.4237 (3)0.0557 (12)
H6N0.32090.19490.42510.067*
C10.3494 (5)0.0295 (4)0.1906 (3)0.0469 (13)
C20.4071 (6)−0.0031 (4)0.2565 (3)0.0482 (13)
C30.3189 (7)−0.0040 (4)0.3370 (3)0.0579 (15)
C40.1815 (7)0.0235 (4)0.3527 (4)0.0704 (19)
H40.12510.02170.40670.085*
C50.1303 (6)0.0533 (5)0.2873 (5)0.0723 (19)
C60.2116 (6)0.0578 (4)0.2078 (4)0.0598 (16)
H6B0.17400.08010.16460.072*
C70.4418 (5)0.0291 (4)0.1042 (3)0.0483 (13)
H7A0.4333−0.03420.08190.058*
H7B0.41190.08540.07020.058*
C80.6281 (5)−0.0394 (4)0.1557 (3)0.0407 (12)
H80.7206−0.02540.15490.049*
C90.6166 (6)0.1452 (4)0.1032 (4)0.0569 (15)
H90.54230.17580.14620.068*
C100.6231 (9)0.2061 (5)0.0216 (5)0.097 (3)
H10A0.53570.20640.01020.116*
H10B0.69120.1731−0.02210.116*
C110.6590 (10)0.3179 (6)0.0215 (6)0.111 (3)
H11A0.66490.3539−0.03240.133*
H11B0.58730.35280.06220.133*
C120.7856 (8)0.3205 (5)0.0402 (4)0.078 (2)
H120.85770.2879−0.00270.093*
C130.7829 (8)0.2642 (5)0.1224 (5)0.086 (2)
H13A0.71520.29780.16590.103*
H13B0.87110.26560.13250.103*
C140.7484 (7)0.1518 (5)0.1241 (4)0.0737 (19)
H14A0.82160.11650.08470.088*
H14B0.74170.11760.17870.088*
C150.6360 (5)−0.1458 (4)0.1260 (3)0.0410 (12)
C160.5412 (5)−0.2159 (4)0.1637 (3)0.0465 (13)
H160.4664−0.19730.20690.056*
C170.5551 (6)−0.3135 (4)0.1386 (3)0.0511 (13)
C180.6655 (6)−0.3457 (5)0.0763 (4)0.0662 (17)
H180.6752−0.41230.06070.079*
C190.7607 (6)−0.2758 (5)0.0380 (4)0.0614 (16)
H190.8361−0.2950−0.00450.074*
C200.7458 (5)−0.1784 (4)0.0618 (3)0.0487 (13)
C210.3193 (5)0.4363 (4)0.4205 (3)0.0445 (12)
C220.3731 (5)0.3365 (4)0.4085 (3)0.0443 (12)
C230.5137 (5)0.3210 (4)0.3792 (3)0.0481 (13)
C240.5984 (6)0.4014 (5)0.3633 (3)0.0586 (16)
H240.69250.38950.34400.070*
C250.5415 (6)0.4989 (5)0.3765 (4)0.0595 (15)
C260.4024 (6)0.5159 (4)0.4057 (3)0.0539 (14)
H260.36470.58200.41550.065*
C270.1651 (5)0.4519 (4)0.4489 (3)0.0449 (12)
H27A0.13380.44070.50870.054*
H27B0.13780.52200.43310.054*
C280.1395 (5)0.2766 (4)0.4373 (3)0.0463 (13)
H280.11100.23190.40340.056*
O60.0678 (19)0.4493 (13)0.0811 (8)0.057 (4)0.343 (12)
H6−0.00510.44250.06960.085*0.343 (12)
C290.1191 (7)0.4085 (5)0.3235 (3)0.079 (2)0.343 (12)
H29A0.17920.46340.32100.095*0.343 (12)
C300.0096 (19)0.4808 (16)0.3083 (8)0.052 (8)0.343 (12)
H30A0.02730.54810.31970.062*0.343 (12)
H30B−0.07480.46160.34850.062*0.343 (12)
C31−0.0137 (17)0.4906 (19)0.2262 (8)0.067 (6)0.343 (12)
H31A−0.04120.56170.21370.080*0.343 (12)
H31B−0.08960.45020.22900.080*0.343 (12)
C320.1012 (18)0.4595 (13)0.1567 (7)0.065 (6)0.343 (12)
H32A0.16180.51620.14370.078*0.343 (12)
C330.1854 (18)0.3684 (13)0.1758 (7)0.053 (6)0.343 (12)
H33A0.13980.30800.17310.063*0.343 (12)
H33B0.27130.36710.13270.063*0.343 (12)
C340.2156 (15)0.3599 (13)0.2562 (6)0.057 (5)0.343 (12)
H34A0.22570.28760.27370.068*0.343 (12)
H34B0.30320.38810.24760.068*0.343 (12)
O6'0.0198 (12)0.4810 (10)0.0975 (6)0.095 (4)0.657 (12)
H6'−0.04360.46420.08020.142*0.657 (12)
C29'0.1191 (7)0.4085 (5)0.3235 (3)0.079 (2)0.657 (12)
H29B0.21380.42770.30260.095*0.657 (12)
C30'0.0385 (12)0.5058 (7)0.3093 (5)0.049 (3)0.657 (12)
H30C0.07380.56100.32920.059*0.657 (12)
H30D−0.05520.49920.34250.059*0.657 (12)
C31'0.0389 (12)0.5356 (7)0.2214 (5)0.067 (3)0.657 (12)
H31C−0.03140.58970.21980.081*0.657 (12)
H31D0.12620.56190.19080.081*0.657 (12)
C32'0.0143 (13)0.4461 (8)0.1814 (6)0.081 (4)0.657 (12)
H32B−0.07640.42240.21010.098*0.657 (12)
C33'0.1193 (15)0.3608 (7)0.1855 (5)0.077 (4)0.657 (12)
H33C0.20910.38390.15650.092*0.657 (12)
H33D0.10370.30370.15830.092*0.657 (12)
C34'0.1142 (13)0.3259 (6)0.2735 (5)0.072 (3)0.657 (12)
H34C0.03090.29120.29890.087*0.657 (12)
H34D0.19020.27640.27390.087*0.657 (12)
C350.0602 (5)0.2507 (4)0.5269 (3)0.0420 (12)
C360.1226 (6)0.2241 (4)0.5892 (4)0.0519 (14)
H360.21720.22050.57690.062*
C370.0451 (7)0.2028 (4)0.6695 (4)0.0570 (15)
C38−0.0942 (7)0.2086 (4)0.6919 (4)0.0617 (16)
H38−0.14440.19640.74690.074*
C39−0.1569 (6)0.2328 (4)0.6310 (3)0.0516 (14)
H39−0.25150.23600.64420.062*
C40−0.0820 (5)0.2523 (4)0.5505 (3)0.0435 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1211 (7)0.0938 (6)0.0491 (4)−0.0380 (5)−0.0139 (4)0.0028 (3)
Br20.0488 (4)0.0931 (6)0.1853 (10)0.0068 (4)0.0052 (5)−0.0404 (6)
Br30.0649 (4)0.0829 (5)0.1281 (7)−0.0302 (4)−0.0261 (4)0.0094 (5)
Br40.0500 (4)0.0687 (4)0.0959 (5)0.0196 (3)−0.0086 (3)−0.0173 (4)
Cl10.0529 (9)0.0799 (11)0.0661 (10)−0.0119 (8)0.0041 (8)−0.0084 (8)
Cl20.0496 (8)0.0840 (11)0.0619 (9)−0.0129 (7)−0.0264 (7)−0.0010 (8)
O10.120 (5)0.060 (3)0.193 (7)−0.028 (3)0.019 (4)−0.048 (4)
O20.073 (3)0.074 (3)0.120 (4)−0.024 (3)0.013 (3)−0.020 (3)
O30.106 (4)0.048 (3)0.083 (3)−0.029 (2)−0.010 (3)0.002 (2)
O40.096 (4)0.143 (5)0.134 (5)−0.020 (4)−0.076 (4)0.052 (4)
O50.147 (6)0.219 (8)0.072 (4)−0.013 (5)−0.056 (4)0.040 (4)
N10.073 (4)0.048 (3)0.094 (4)−0.014 (3)−0.011 (3)−0.012 (3)
N20.046 (2)0.038 (2)0.048 (3)−0.0040 (19)−0.015 (2)−0.004 (2)
N30.055 (3)0.051 (3)0.037 (2)0.004 (2)−0.017 (2)−0.006 (2)
N40.099 (5)0.081 (4)0.085 (5)−0.012 (4)−0.052 (4)0.022 (3)
N50.040 (2)0.045 (3)0.042 (2)0.0008 (19)−0.0101 (19)−0.0040 (19)
N60.042 (3)0.038 (3)0.079 (3)0.006 (2)−0.005 (2)−0.010 (2)
C10.047 (3)0.036 (3)0.057 (3)−0.001 (2)−0.014 (3)−0.009 (3)
C20.059 (3)0.031 (3)0.053 (3)−0.008 (2)−0.008 (3)−0.010 (2)
C30.076 (4)0.040 (3)0.050 (3)−0.014 (3)−0.002 (3)−0.006 (3)
C40.068 (4)0.050 (4)0.072 (5)−0.015 (3)0.023 (4)−0.021 (3)
C50.049 (4)0.055 (4)0.101 (6)0.001 (3)0.003 (4)−0.022 (4)
C60.052 (3)0.044 (3)0.084 (5)0.002 (3)−0.015 (3)−0.016 (3)
C70.049 (3)0.043 (3)0.056 (3)0.002 (2)−0.021 (3)−0.004 (3)
C80.040 (3)0.040 (3)0.044 (3)−0.001 (2)−0.016 (2)−0.003 (2)
C90.063 (4)0.048 (3)0.063 (4)−0.005 (3)−0.023 (3)−0.001 (3)
C100.142 (7)0.068 (5)0.106 (6)−0.036 (5)−0.080 (6)0.023 (4)
C110.148 (8)0.072 (5)0.141 (8)−0.035 (5)−0.094 (7)0.039 (5)
C120.099 (5)0.060 (4)0.070 (4)−0.031 (4)−0.012 (4)0.005 (3)
C130.110 (6)0.073 (5)0.088 (5)−0.035 (4)−0.045 (5)0.004 (4)
C140.079 (5)0.067 (4)0.082 (5)−0.022 (4)−0.037 (4)0.014 (4)
C150.043 (3)0.041 (3)0.040 (3)0.001 (2)−0.014 (2)−0.001 (2)
C160.047 (3)0.044 (3)0.048 (3)0.001 (2)−0.013 (3)−0.005 (2)
C170.052 (3)0.041 (3)0.059 (4)−0.002 (3)−0.014 (3)−0.006 (3)
C180.070 (4)0.047 (4)0.078 (4)0.007 (3)−0.012 (4)−0.021 (3)
C190.056 (4)0.065 (4)0.052 (4)0.003 (3)0.004 (3)−0.018 (3)
C200.043 (3)0.051 (3)0.048 (3)0.000 (2)−0.008 (3)−0.004 (3)
C210.044 (3)0.042 (3)0.046 (3)0.002 (2)−0.014 (2)0.000 (2)
C220.045 (3)0.042 (3)0.044 (3)0.003 (2)−0.013 (2)0.001 (2)
C230.041 (3)0.056 (3)0.044 (3)0.004 (3)−0.010 (2)−0.003 (3)
C240.036 (3)0.081 (5)0.058 (4)−0.001 (3)−0.016 (3)0.003 (3)
C250.049 (3)0.062 (4)0.066 (4)−0.012 (3)−0.016 (3)0.004 (3)
C260.053 (3)0.050 (3)0.058 (4)−0.005 (3)−0.014 (3)−0.003 (3)
C270.041 (3)0.036 (3)0.052 (3)−0.001 (2)−0.006 (3)−0.004 (2)
C280.042 (3)0.043 (3)0.054 (3)−0.002 (2)−0.013 (3)−0.007 (3)
O60.080 (8)0.053 (7)0.038 (7)0.013 (6)−0.021 (6)−0.010 (5)
C290.095 (5)0.086 (5)0.056 (4)0.039 (4)−0.028 (4)−0.021 (4)
C300.055 (10)0.053 (10)0.045 (10)0.000 (8)−0.011 (7)−0.007 (7)
C310.072 (10)0.074 (10)0.056 (9)0.013 (8)−0.027 (8)−0.002 (8)
C320.099 (18)0.061 (13)0.038 (11)0.000 (12)−0.025 (12)−0.005 (9)
C330.040 (11)0.080 (14)0.038 (10)−0.002 (9)−0.010 (8)−0.009 (9)
C340.045 (10)0.070 (12)0.053 (11)0.010 (9)−0.013 (9)−0.009 (9)
O6'0.114 (7)0.125 (8)0.053 (5)−0.037 (6)−0.030 (5)0.003 (5)
C29'0.095 (5)0.086 (5)0.056 (4)0.039 (4)−0.028 (4)−0.021 (4)
C30'0.060 (6)0.043 (6)0.050 (6)−0.006 (5)−0.021 (5)−0.009 (4)
C31'0.066 (6)0.076 (6)0.063 (6)−0.006 (5)−0.027 (5)0.004 (5)
C32'0.079 (9)0.139 (12)0.029 (6)−0.050 (9)−0.015 (6)0.020 (6)
C33'0.103 (9)0.077 (7)0.047 (6)−0.022 (6)−0.009 (6)−0.011 (5)
C34'0.092 (7)0.061 (6)0.067 (6)−0.012 (5)−0.027 (5)0.003 (5)
C350.042 (3)0.036 (3)0.050 (3)0.002 (2)−0.017 (3)−0.009 (2)
C360.046 (3)0.041 (3)0.069 (4)0.003 (2)−0.022 (3)0.001 (3)
C370.075 (4)0.046 (3)0.058 (4)−0.002 (3)−0.036 (3)0.007 (3)
C380.075 (4)0.050 (4)0.055 (4)−0.005 (3)−0.013 (3)0.004 (3)
C390.049 (3)0.054 (3)0.050 (3)−0.002 (3)−0.014 (3)0.000 (3)
C400.044 (3)0.040 (3)0.051 (3)−0.001 (2)−0.020 (3)−0.005 (2)

Geometric parameters (Å, °)

Br1—C31.897 (6)C18—H180.9300
Br2—C51.904 (6)C19—C201.365 (8)
Br3—C251.890 (6)C19—H190.9300
Br4—C231.893 (5)C21—C261.367 (7)
Cl1—C201.737 (5)C21—C221.387 (7)
Cl2—C401.729 (5)C21—C271.517 (7)
O1—N11.201 (6)C22—C231.388 (7)
O2—N11.204 (7)C23—C241.384 (8)
O3—C121.441 (7)C24—C251.373 (8)
O3—H30.8401C24—H240.9300
O4—N41.186 (8)C25—C261.375 (8)
O5—N41.210 (8)C26—H260.9300
N1—C171.460 (7)C27—H27A0.9700
N2—C71.461 (6)C27—H27B0.9700
N2—C81.464 (6)C28—C351.519 (7)
N2—C91.487 (7)C28—H280.9800
N3—C21.371 (7)O6—C321.439 (10)
N3—C81.444 (6)O6—H60.8401
N3—H3N0.8600O6—H6'1.1466
N4—C371.472 (8)C29—C341.442 (8)
N5—C281.448 (6)C29—C301.466 (8)
N5—C271.460 (6)C29—H29A0.9800
N5—C291.470 (7)C30—C311.468 (9)
N6—C221.383 (6)C30—H30A0.9700
N6—C281.467 (6)C30—H30B0.9700
N6—H6N0.8600C31—C321.469 (9)
C1—C61.383 (7)C31—H31A0.9700
C1—C21.416 (7)C31—H31B0.9700
C1—C71.499 (7)C32—C331.474 (9)
C2—C31.403 (8)C32—H32A0.9800
C3—C41.379 (9)C33—C341.470 (9)
C4—C51.364 (9)C33—H33A0.9700
C4—H40.9300C33—H33B0.9700
C5—C61.363 (9)C34—H34A0.9700
C6—H6B0.9300C34—H34B0.9700
C7—H7A0.9700O6'—C32'1.432 (12)
C7—H7B0.9700O6'—H60.8290
C8—C151.525 (7)O6'—H6'0.8401
C8—H80.9800C30'—C31'1.496 (7)
C9—C141.505 (8)C30'—H30C0.9700
C9—C101.507 (8)C30'—H30D0.9700
C9—H90.9800C31'—C32'1.494 (7)
C10—C111.548 (9)C31'—H31C0.9700
C10—H10A0.9700C31'—H31D0.9700
C10—H10B0.9700C32'—C33'1.492 (8)
C11—C121.427 (10)C32'—H32B0.9800
C11—H11A0.9700C33'—C34'1.497 (7)
C11—H11B0.9700C33'—H33C0.9700
C12—C131.497 (9)C33'—H33D0.9700
C12—H120.9800C34'—H34C0.9700
C13—C141.545 (9)C34'—H34D0.9700
C13—H13A0.9700C35—C361.382 (7)
C13—H13B0.9700C35—C401.397 (7)
C14—H14A0.9700C36—C371.377 (8)
C14—H14B0.9700C36—H360.9300
C15—C161.372 (7)C37—C381.367 (8)
C15—C201.394 (7)C38—C391.360 (8)
C16—C171.376 (7)C38—H380.9300
C16—H160.9300C39—C401.369 (7)
C17—C181.378 (8)C39—H390.9300
C18—C191.375 (8)
C12—O3—H3118.6C24—C23—C22121.7 (5)
O1—N1—O2122.5 (6)C24—C23—Br4119.4 (4)
O1—N1—C17118.7 (6)C22—C23—Br4118.9 (4)
O2—N1—C17118.8 (5)C25—C24—C23119.0 (5)
C7—N2—C8109.3 (4)C25—C24—H24120.5
C7—N2—C9112.8 (4)C23—C24—H24120.5
C8—N2—C9115.5 (4)C24—C25—C26120.2 (5)
C2—N3—C8121.6 (4)C24—C25—Br3120.6 (4)
C2—N3—H3N119.2C26—C25—Br3119.1 (5)
C8—N3—H3N119.2C21—C26—C25120.5 (5)
O4—N4—O5123.2 (7)C21—C26—H26119.8
O4—N4—C37118.6 (7)C25—C26—H26119.8
O5—N4—C37118.1 (7)N5—C27—C21110.9 (4)
C28—N5—C27109.7 (4)N5—C27—H27A109.5
C28—N5—C29117.3 (4)C21—C27—H27A109.5
C27—N5—C29112.7 (4)N5—C27—H27B109.5
C22—N6—C28121.7 (4)C21—C27—H27B109.5
C22—N6—H6N119.2H27A—C27—H27B108.1
C28—N6—H6N119.2N5—C28—N6112.7 (4)
C6—C1—C2119.6 (5)N5—C28—C35109.0 (4)
C6—C1—C7122.8 (5)N6—C28—C35112.2 (4)
C2—C1—C7117.6 (5)N5—C28—H28107.6
N3—C2—C3123.3 (5)N6—C28—H28107.6
N3—C2—C1119.7 (5)C35—C28—H28107.6
C3—C2—C1117.0 (5)C32—O6—H6134.0
C4—C3—C2122.4 (6)C32—O6—H6'118.5
C4—C3—Br1119.0 (5)H6—O6—H6'20.8
C2—C3—Br1118.5 (5)C34—C29—C30120.7 (6)
C5—C4—C3118.5 (6)C34—C29—N5126.4 (6)
C5—C4—H4120.8C30—C29—N5112.1 (6)
C3—C4—H4120.8C34—C29—H29A93.0
C6—C5—C4121.6 (6)C30—C29—H29A93.0
C6—C5—Br2119.5 (6)N5—C29—H29A93.0
C4—C5—Br2118.8 (5)C29—C30—C31118.7 (7)
C5—C6—C1120.8 (6)C29—C30—H30A107.6
C5—C6—H6B119.6C31—C30—H30A107.6
C1—C6—H6B119.6C29—C30—H30B107.6
N2—C7—C1114.2 (4)C31—C30—H30B107.6
N2—C7—H7A108.7H30A—C30—H30B107.1
C1—C7—H7A108.7C30—C31—C32117.0 (8)
N2—C7—H7B108.7C30—C31—H31A108.0
C1—C7—H7B108.7C32—C31—H31A108.1
H7A—C7—H7B107.6C30—C31—H31B108.0
N3—C8—N2111.8 (4)C32—C31—H31B108.0
N3—C8—C15113.2 (4)H31A—C31—H31B107.3
N2—C8—C15110.3 (4)O6—C32—C31115.5 (14)
N3—C8—H8107.1O6—C32—C33109.5 (12)
N2—C8—H8107.1C31—C32—C33115.2 (9)
C15—C8—H8107.1O6—C32—H32A105.1
N2—C9—C14113.4 (5)C31—C32—H32A105.1
N2—C9—C10108.7 (5)C33—C32—H32A105.1
C14—C9—C10109.1 (5)C34—C33—C32117.0 (8)
N2—C9—H9108.5C34—C33—H33A108.1
C14—C9—H9108.5C32—C33—H33A108.1
C10—C9—H9108.5C34—C33—H33B108.1
C9—C10—C11111.9 (6)C32—C33—H33B108.1
C9—C10—H10A109.2H33A—C33—H33B107.3
C11—C10—H10A109.2C29—C34—C33118.0 (7)
C9—C10—H10B109.2C29—C34—H34A107.8
C11—C10—H10B109.2C33—C34—H34A107.8
H10A—C10—H10B107.9C29—C34—H34B107.8
C12—C11—C10110.9 (6)C33—C34—H34B107.8
C12—C11—H11A109.5H34A—C34—H34B107.1
C10—C11—H11A109.5C32'—O6'—H6118.2
C12—C11—H11B109.5C32'—O6'—H6'116.1
C10—C11—H11B109.5H6—O6'—H6'32.6
H11A—C11—H11B108.1C31'—C30'—H30C108.4
C11—C12—O3111.2 (6)C31'—C30'—H30D108.4
C11—C12—C13111.6 (6)H30C—C30'—H30D107.5
O3—C12—C13108.1 (5)C32'—C31'—C30'111.1 (7)
C11—C12—H12108.6C32'—C31'—H31C109.4
O3—C12—H12108.6C30'—C31'—H31C109.4
C13—C12—H12108.6C32'—C31'—H31D109.4
C12—C13—C14110.3 (5)C30'—C31'—H31D109.4
C12—C13—H13A109.6H31C—C31'—H31D108.0
C14—C13—H13A109.6O6'—C32'—C33'111.3 (9)
C12—C13—H13B109.6O6'—C32'—C31'107.2 (9)
C14—C13—H13B109.6C33'—C32'—C31'110.1 (7)
H13A—C13—H13B108.1O6'—C32'—H32B109.4
C9—C14—C13111.8 (5)C33'—C32'—H32B109.4
C9—C14—H14A109.3C31'—C32'—H32B109.4
C13—C14—H14A109.3C32'—C33'—C34'110.9 (7)
C9—C14—H14B109.3C32'—C33'—H33C109.5
C13—C14—H14B109.3C34'—C33'—H33C109.5
H14A—C14—H14B107.9C32'—C33'—H33D109.5
C16—C15—C20116.8 (5)C34'—C33'—H33D109.5
C16—C15—C8122.2 (5)H33C—C33'—H33D108.1
C20—C15—C8120.8 (5)C33'—C34'—H34C108.7
C15—C16—C17120.9 (5)C33'—C34'—H34D108.7
C15—C16—H16119.5H34C—C34'—H34D107.6
C17—C16—H16119.5C36—C35—C40116.3 (5)
C16—C17—C18121.8 (5)C36—C35—C28122.9 (5)
C16—C17—N1119.2 (5)C40—C35—C28120.9 (4)
C18—C17—N1119.0 (5)C37—C36—C35120.2 (5)
C19—C18—C17117.6 (5)C37—C36—H36119.9
C19—C18—H18121.2C35—C36—H36119.9
C17—C18—H18121.2C38—C37—C36122.7 (5)
C20—C19—C18120.7 (5)C38—C37—N4119.3 (6)
C20—C19—H19119.7C36—C37—N4118.0 (6)
C18—C19—H19119.7C39—C38—C37117.7 (6)
C19—C20—C15122.1 (5)C39—C38—H38121.1
C19—C20—Cl1117.5 (4)C37—C38—H38121.1
C15—C20—Cl1120.4 (4)C38—C39—C40120.7 (5)
C26—C21—C22121.0 (5)C38—C39—H39119.7
C26—C21—C27122.4 (5)C40—C39—H39119.7
C22—C21—C27116.7 (5)C39—C40—C35122.4 (5)
N6—C22—C21120.0 (5)C39—C40—Cl2116.8 (4)
N6—C22—C23122.3 (5)C35—C40—Cl2120.8 (4)
C21—C22—C23117.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3N···O4i0.862.332.942 (7)129
O3—H3···O6'ii0.841.892.713 (12)166
O6—H6···O3iii0.842.042.877 (17)179
O6'—H6'···O3iii0.841.852.694 (10)179

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5014).

References

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