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The title compound, C24H18Br2N4O2·H2O, forms a supra­molecular structure via N—H...O, O—H...O and C—H...O hydrogen bonds. In the crystal structure, the water molecule serves as a bifurcated hydrogen-bond acceptor and as a hydrogen-bond donor.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011871/sj2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011871/sj2032Isup2.hkl
Contains datablock I

CCDC reference: 608491

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.053
  • wR factor = 0.136
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.91 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.46 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.914 Tmax scaled 0.488 Tmin scaled 0.377
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

6,9-Dibromo-2a,10b-diphenyl-2a,5,10,10b-tetrahydro-2H,3H-2,3,4a, 10a-tetraaza-benzo[g]cyclopenta[cd]azulene-1,4-dione hydrate top
Crystal data top
C24H18Br2N4O2·H2OF(000) = 1144
Mr = 572.26Dx = 1.666 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3096 reflections
a = 13.066 (2) Åθ = 2.3–21.7°
b = 9.9260 (15) ŵ = 3.59 mm1
c = 18.351 (3) ÅT = 292 K
β = 106.539 (3)°Prism, colorless
V = 2281.5 (6) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
5151 independent reflections
Radiation source: fine-focus sealed tube3218 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick 1997)
h = 1316
Tmin = 0.412, Tmax = 0.534k = 1212
14118 measured reflectionsl = 2323
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0625P)2]
where P = (Fo2 + 2Fc2)/3
5151 reflections(Δ/σ)max < 0.001
306 parametersΔρmax = 0.68 e Å3
51 restraintsΔρmin = 0.56 e Å3
Special details top

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
Br10.11556 (7)0.73670 (9)0.39639 (5)0.0716 (4)
Br20.03296 (7)0.10457 (10)0.37718 (5)0.0776 (4)
C10.1132 (5)0.4707 (7)0.4607 (3)0.0365 (15)
C20.0761 (5)0.5518 (8)0.3963 (4)0.0484 (18)
C30.0064 (6)0.5019 (10)0.3297 (4)0.061 (2)
H30.01900.55820.28800.073*
C40.0246 (6)0.3701 (10)0.3258 (4)0.062 (2)
H40.07100.33610.28130.075*
C50.0135 (5)0.2873 (8)0.3883 (4)0.0485 (18)
C60.0829 (4)0.3355 (7)0.4559 (3)0.0369 (15)
C70.1197 (5)0.2437 (6)0.5247 (4)0.0363 (14)
H7A0.08930.27590.56400.044*
H7B0.09190.15390.51040.044*
C80.1812 (4)0.5298 (6)0.5352 (3)0.0347 (14)
H8A0.19150.62500.52770.042*
H8B0.14210.52210.57270.042*
C90.2955 (5)0.1307 (6)0.5429 (3)0.0346 (14)
C100.3638 (5)0.4824 (6)0.5300 (3)0.0340 (14)
C110.2964 (4)0.3401 (6)0.6051 (3)0.0283 (12)
C120.2688 (4)0.3493 (6)0.6797 (3)0.0321 (13)
C130.2240 (5)0.2414 (7)0.7077 (4)0.0437 (16)
H130.20350.16460.67810.052*
C140.2096 (6)0.2479 (9)0.7798 (4)0.060 (2)
H140.18100.17460.79890.072*
C150.2371 (6)0.3603 (10)0.8222 (4)0.069 (2)
H150.22690.36350.87030.083*
C160.2797 (6)0.4699 (9)0.7961 (4)0.063 (2)
H160.29790.54680.82600.075*
C170.2954 (5)0.4647 (7)0.7231 (4)0.0450 (16)
H170.32360.53860.70430.054*
C180.4156 (4)0.2943 (6)0.6099 (3)0.0314 (13)
C190.4986 (5)0.3037 (7)0.6861 (4)0.0382 (15)
C200.4872 (6)0.2300 (8)0.7464 (4)0.058 (2)
H200.43100.16930.73930.069*
C210.5589 (8)0.2451 (10)0.8182 (5)0.074 (3)
H210.54760.19870.85930.089*
C220.6447 (9)0.3264 (10)0.8289 (5)0.087 (3)
H220.69280.33580.87690.104*
C230.6598 (8)0.3942 (10)0.7687 (6)0.098 (4)
H230.72050.44710.77530.118*
C240.5863 (6)0.3859 (8)0.6972 (5)0.065 (2)
H240.59640.43600.65700.078*
N10.2351 (4)0.2352 (5)0.5563 (3)0.0314 (11)
N20.2860 (4)0.4671 (5)0.5661 (3)0.0302 (11)
N30.3992 (4)0.1563 (5)0.5825 (3)0.0368 (12)
H3C0.44930.09720.59040.044*
N40.4358 (4)0.3848 (5)0.5532 (3)0.0381 (13)
H4A0.49020.37600.53590.046*
O10.2612 (3)0.0326 (4)0.5041 (2)0.0448 (11)
O20.3659 (3)0.5750 (4)0.4854 (3)0.0448 (11)
O30.4032 (4)0.8572 (6)0.4646 (4)0.0690 (14)
H3B0.362 (4)0.919 (4)0.476 (3)0.0500 (18)*
H3A0.380 (5)0.779 (3)0.472 (4)0.0500 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0554 (5)0.0762 (6)0.0875 (7)0.0164 (4)0.0272 (5)0.0447 (5)
Br20.0617 (6)0.0907 (7)0.0696 (6)0.0180 (5)0.0013 (4)0.0267 (5)
C10.028 (3)0.051 (4)0.037 (3)0.010 (3)0.019 (3)0.005 (3)
C20.037 (4)0.069 (5)0.046 (4)0.019 (3)0.022 (3)0.018 (4)
C30.048 (4)0.100 (7)0.037 (4)0.026 (4)0.016 (3)0.015 (4)
C40.042 (4)0.102 (7)0.037 (4)0.021 (4)0.002 (3)0.009 (4)
C50.031 (4)0.070 (5)0.043 (4)0.009 (3)0.010 (3)0.009 (4)
C60.023 (3)0.055 (4)0.035 (3)0.010 (3)0.012 (3)0.002 (3)
C70.027 (3)0.041 (4)0.042 (3)0.004 (3)0.011 (3)0.003 (3)
C80.029 (3)0.039 (4)0.040 (3)0.010 (3)0.015 (3)0.008 (3)
C90.043 (4)0.036 (4)0.028 (3)0.007 (3)0.014 (3)0.006 (3)
C100.030 (3)0.038 (4)0.036 (3)0.000 (3)0.013 (3)0.001 (3)
C110.023 (3)0.030 (3)0.033 (3)0.000 (2)0.010 (2)0.002 (2)
C120.025 (3)0.043 (4)0.029 (3)0.006 (3)0.009 (2)0.004 (3)
C130.040 (4)0.052 (4)0.041 (4)0.001 (3)0.015 (3)0.006 (3)
C140.057 (5)0.083 (6)0.048 (4)0.005 (4)0.028 (4)0.019 (4)
C150.059 (5)0.116 (7)0.038 (4)0.001 (5)0.025 (4)0.006 (5)
C160.061 (5)0.087 (6)0.040 (4)0.001 (4)0.014 (4)0.019 (4)
C170.043 (4)0.053 (4)0.041 (4)0.000 (3)0.014 (3)0.001 (3)
C180.027 (3)0.036 (3)0.036 (3)0.005 (2)0.016 (3)0.005 (3)
C190.030 (3)0.043 (4)0.040 (4)0.009 (3)0.007 (3)0.000 (3)
C200.039 (4)0.083 (6)0.049 (4)0.011 (4)0.009 (3)0.022 (4)
C210.079 (6)0.097 (7)0.044 (4)0.039 (5)0.014 (4)0.015 (4)
C220.107 (8)0.070 (6)0.057 (5)0.026 (6)0.019 (5)0.019 (5)
C230.081 (6)0.070 (6)0.105 (7)0.019 (5)0.037 (6)0.005 (6)
C240.059 (5)0.056 (5)0.065 (5)0.008 (4)0.006 (4)0.003 (4)
N10.027 (3)0.035 (3)0.033 (3)0.002 (2)0.009 (2)0.001 (2)
N20.024 (2)0.035 (3)0.035 (3)0.005 (2)0.014 (2)0.005 (2)
N30.030 (3)0.035 (3)0.045 (3)0.010 (2)0.009 (2)0.001 (2)
N40.030 (3)0.047 (3)0.044 (3)0.010 (2)0.021 (2)0.015 (2)
O10.048 (3)0.040 (3)0.046 (3)0.005 (2)0.012 (2)0.010 (2)
O20.042 (3)0.046 (3)0.054 (3)0.008 (2)0.026 (2)0.022 (2)
O30.0637 (17)0.0547 (18)0.1056 (18)0.0114 (11)0.0516 (13)0.0077 (11)
Geometric parameters (Å, º) top
Br1—C21.906 (8)C12—C131.387 (9)
Br2—C51.905 (8)C13—C141.391 (10)
C1—C61.395 (9)C13—H130.9300
C1—C21.397 (8)C14—C151.349 (11)
C1—C81.521 (8)C14—H140.9300
C2—C31.391 (10)C15—C161.369 (11)
C3—C41.366 (11)C15—H150.9300
C3—H30.9300C16—C171.413 (9)
C4—C51.384 (10)C16—H160.9300
C4—H40.9300C17—H170.9300
C5—C61.396 (9)C18—N31.453 (8)
C6—C71.520 (9)C18—N41.456 (7)
C7—N11.455 (7)C18—C191.509 (8)
C7—H7A0.9700C19—C201.371 (10)
C7—H7B0.9700C19—C241.373 (10)
C8—N21.463 (7)C20—C211.390 (11)
C8—H8A0.9700C20—H200.9300
C8—H8B0.9700C21—C221.350 (13)
C9—O11.214 (7)C21—H210.9300
C9—N31.367 (8)C22—C231.355 (14)
C9—N11.368 (7)C22—H220.9300
C10—O21.236 (7)C23—C241.390 (12)
C10—N41.333 (7)C23—H230.9300
C10—N21.371 (7)C24—H240.9300
C11—N21.437 (7)N3—H3C0.8600
C11—N11.455 (7)N4—H4A0.8600
C11—C121.515 (8)O3—H3B0.88 (5)
C11—C181.600 (7)O3—H3A0.86 (4)
C12—C171.382 (9)
C6—C1—C2118.5 (6)C15—C14—H14120.0
C6—C1—C8120.7 (5)C13—C14—H14120.0
C2—C1—C8120.7 (6)C14—C15—C16121.6 (7)
C3—C2—C1121.3 (7)C14—C15—H15119.2
C3—C2—Br1116.9 (6)C16—C15—H15119.2
C1—C2—Br1121.7 (5)C15—C16—C17119.1 (7)
C4—C3—C2119.9 (7)C15—C16—H16120.5
C4—C3—H3120.0C17—C16—H16120.5
C2—C3—H3120.0C12—C17—C16119.7 (7)
C3—C4—C5119.5 (7)C12—C17—H17120.1
C3—C4—H4120.2C16—C17—H17120.1
C5—C4—H4120.2N3—C18—N4111.9 (5)
C4—C5—C6121.5 (7)N3—C18—C19112.0 (5)
C4—C5—Br2116.6 (6)N4—C18—C19113.3 (5)
C6—C5—Br2121.9 (5)N3—C18—C11101.7 (4)
C1—C6—C5119.1 (6)N4—C18—C1199.0 (4)
C1—C6—C7120.5 (5)C19—C18—C11117.8 (4)
C5—C6—C7120.3 (6)C20—C19—C24118.4 (7)
N1—C7—C6114.4 (5)C20—C19—C18120.0 (6)
N1—C7—H7A108.7C24—C19—C18121.6 (6)
C6—C7—H7A108.7C19—C20—C21120.6 (8)
N1—C7—H7B108.7C19—C20—H20119.7
C6—C7—H7B108.7C21—C20—H20119.7
H7A—C7—H7B107.6C22—C21—C20120.6 (9)
N2—C8—C1115.3 (5)C22—C21—H21119.7
N2—C8—H8A108.5C20—C21—H21119.7
C1—C8—H8A108.5C21—C22—C23119.1 (8)
N2—C8—H8B108.5C21—C22—H22120.4
C1—C8—H8B108.5C23—C22—H22120.4
H8A—C8—H8B107.5C22—C23—C24121.2 (9)
O1—C9—N3127.3 (6)C22—C23—H23119.4
O1—C9—N1125.3 (6)C24—C23—H23119.4
N3—C9—N1107.4 (5)C19—C24—C23119.9 (9)
O2—C10—N4127.2 (5)C19—C24—H24120.0
O2—C10—N2124.2 (5)C23—C24—H24120.0
N4—C10—N2108.6 (5)C9—N1—C7123.9 (5)
N2—C11—N1111.4 (4)C9—N1—C11114.1 (5)
N2—C11—C12112.6 (5)C7—N1—C11122.0 (4)
N1—C11—C12111.6 (5)C10—N2—C11111.1 (4)
N2—C11—C18103.3 (4)C10—N2—C8120.5 (5)
N1—C11—C18100.8 (4)C11—N2—C8120.7 (4)
C12—C11—C18116.4 (4)C9—N3—C18112.6 (5)
C17—C12—C13119.4 (6)C9—N3—H3C123.7
C17—C12—C11119.0 (5)C18—N3—H3C123.7
C13—C12—C11121.5 (6)C10—N4—C18114.9 (5)
C12—C13—C14120.2 (7)C10—N4—H4A122.5
C12—C13—H13119.9C18—N4—H4A122.5
C14—C13—H13119.9H3B—O3—H3A109 (4)
C15—C14—C13120.0 (7)
C6—C1—C2—C33.0 (9)C11—C18—C19—C2061.6 (8)
C8—C1—C2—C3174.4 (5)N3—C18—C19—C24124.7 (7)
C6—C1—C2—Br1178.5 (4)N4—C18—C19—C243.1 (8)
C8—C1—C2—Br14.0 (7)C11—C18—C19—C24117.9 (7)
C1—C2—C3—C41.9 (10)C24—C19—C20—C214.2 (11)
Br1—C2—C3—C4179.7 (5)C18—C19—C20—C21175.3 (6)
C2—C3—C4—C50.2 (10)C19—C20—C21—C224.1 (13)
C3—C4—C5—C60.2 (10)C20—C21—C22—C230.5 (14)
C3—C4—C5—Br2179.4 (5)C21—C22—C23—C242.9 (15)
C2—C1—C6—C52.6 (8)C20—C19—C24—C230.9 (12)
C8—C1—C6—C5174.9 (5)C18—C19—C24—C23178.6 (7)
C2—C1—C6—C7179.0 (5)C22—C23—C24—C192.7 (15)
C8—C1—C6—C71.5 (8)O1—C9—N1—C70.8 (9)
C4—C5—C6—C11.0 (9)N3—C9—N1—C7179.1 (5)
Br2—C5—C6—C1179.4 (4)O1—C9—N1—C11179.8 (5)
C4—C5—C6—C7177.4 (6)N3—C9—N1—C111.5 (6)
Br2—C5—C6—C73.0 (8)C6—C7—N1—C9100.4 (6)
C1—C6—C7—N157.5 (7)C6—C7—N1—C1179.0 (7)
C5—C6—C7—N1126.1 (6)N2—C11—N1—C9118.4 (5)
C6—C1—C8—N260.3 (7)C12—C11—N1—C9114.9 (5)
C2—C1—C8—N2122.3 (6)C18—C11—N1—C99.4 (6)
N2—C11—C12—C1735.8 (7)N2—C11—N1—C761.0 (6)
N1—C11—C12—C17161.9 (5)C12—C11—N1—C765.7 (7)
C18—C11—C12—C1783.1 (7)C18—C11—N1—C7170.0 (5)
N2—C11—C12—C13148.4 (6)O2—C10—N2—C11171.3 (6)
N1—C11—C12—C1322.3 (7)N4—C10—N2—C1110.6 (6)
C18—C11—C12—C1392.6 (7)O2—C10—N2—C821.8 (9)
C17—C12—C13—C142.3 (10)N4—C10—N2—C8160.2 (5)
C11—C12—C13—C14173.4 (6)N1—C11—N2—C1090.4 (5)
C12—C13—C14—C151.5 (11)C12—C11—N2—C10143.4 (5)
C13—C14—C15—C160.2 (13)C18—C11—N2—C1017.1 (6)
C14—C15—C16—C170.2 (13)N1—C11—N2—C859.1 (6)
C13—C12—C17—C161.9 (10)C12—C11—N2—C867.1 (6)
C11—C12—C17—C16174.0 (6)C18—C11—N2—C8166.6 (5)
C15—C16—C17—C120.6 (11)C1—C8—N2—C1068.6 (7)
N2—C11—C18—N3130.9 (4)C1—C8—N2—C1178.1 (6)
N1—C11—C18—N315.7 (5)O1—C9—N3—C18168.2 (6)
C12—C11—C18—N3105.2 (5)N1—C9—N3—C1813.6 (6)
N2—C11—C18—N416.2 (5)N4—C18—N3—C986.3 (6)
N1—C11—C18—N499.1 (5)C19—C18—N3—C9145.2 (5)
C12—C11—C18—N4140.1 (5)C11—C18—N3—C918.5 (6)
N2—C11—C18—C19106.2 (6)O2—C10—N4—C18176.2 (6)
N1—C11—C18—C19138.5 (5)N2—C10—N4—C181.7 (7)
C12—C11—C18—C1917.7 (7)N3—C18—N4—C10118.1 (6)
N3—C18—C19—C2055.9 (7)C19—C18—N4—C10114.1 (6)
N4—C18—C19—C20176.4 (6)C11—C18—N4—C1011.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O1i0.932.583.432 (9)152
N4—H4A···O2ii0.862.082.901 (6)158
N3—H3C···O3ii0.862.462.950 (7)117
O3—H3B···O1iii0.88 (5)1.91 (5)2.786 (6)171 (5)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x, y+1, z.
 

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