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In the title compound, C24H22N2O4·3H2O, the two quinoline ring systems are twisted with respect to each other; the dihedral angle is 31.9 (2)°. Adjacent heterocyclic mol­ecules are linked via weak C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053098/xu2173sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053098/xu2173Isup2.hkl
Contains datablock I

CCDC reference: 636839

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.146
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O6 - H6A ... ?
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 700 Deg. PLAT417_ALERT_2_C Short Inter D-H..H-D H5A .. H6A .. 2.12 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 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, 1998); cell refinement: SAINT (Bruker, 1998); 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, 1998); software used to prepare material for publication: SHELXTL.

2,3,10,11-Tetramethoxy-15,16-diazapentaphene trihydrate top
Crystal data top
C24H22N2O4·3H2OZ = 2
Mr = 456.48F(000) = 484
Triclinic, P1Dx = 1.355 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9814 (8) ÅCell parameters from 2051 reflections
b = 11.3775 (11) Åθ = 2.7–24.7°
c = 13.1359 (12) ŵ = 0.10 mm1
α = 74.362 (7)°T = 298 K
β = 81.933 (7)°Prism, brown
γ = 77.998 (7)°0.12 × 0.10 × 0.07 mm
V = 1119.08 (19) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3217 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 1.6°
φ and ω scansh = 910
9347 measured reflectionsk = 1414
5092 independent reflectionsl = 1417
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0734P)2]
where P = (Fo2 + 2Fc2)/3
5092 reflections(Δ/σ)max < 0.001
302 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.20 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
O10.77486 (18)0.54677 (12)0.02474 (9)0.0556 (4)
O20.6902 (2)0.73386 (12)0.05269 (10)0.0635 (4)
O30.09009 (16)0.25993 (11)0.33605 (9)0.0472 (3)
O40.08752 (16)0.34963 (11)0.53722 (9)0.0475 (3)
O50.9252 (2)0.09748 (19)0.05258 (15)0.1043 (6)
H5B0.98360.11080.09550.125*
H5A0.83270.09320.08990.125*
O60.5831 (2)0.09629 (19)0.15534 (15)0.1059 (7)
H6B0.54030.14580.19330.127*
H6A0.56130.13750.09370.127*
O70.1242 (2)0.20350 (16)0.15931 (11)0.0844 (5)
H7B0.19350.17260.20730.101*
H7A0.17060.25420.10950.101*
N10.47068 (18)0.29782 (12)0.26933 (10)0.0380 (3)
N20.29068 (17)0.10237 (12)0.35821 (10)0.0362 (3)
C10.8372 (3)0.44419 (19)0.07052 (16)0.0606 (5)
H1A0.90530.37950.02200.091*
H1B0.90640.47010.13550.091*
H1C0.74170.41370.08490.091*
C20.6783 (2)0.52561 (16)0.06969 (13)0.0429 (4)
C30.6228 (2)0.41794 (16)0.12109 (13)0.0420 (4)
H30.64940.35070.09050.050*
C40.5250 (2)0.40722 (15)0.22051 (12)0.0377 (4)
C50.3915 (2)0.28549 (15)0.36632 (12)0.0353 (4)
C60.3303 (2)0.16763 (15)0.41882 (12)0.0344 (4)
C70.2388 (2)0.00772 (14)0.40686 (12)0.0350 (4)
C80.1927 (2)0.07694 (15)0.34368 (13)0.0379 (4)
H80.19750.04650.27030.046*
C90.1414 (2)0.18767 (15)0.38937 (13)0.0374 (4)
C100.0732 (3)0.21003 (19)0.22530 (14)0.0561 (5)
H10A0.00250.12910.21400.084*
H10B0.02100.26350.19910.084*
H10C0.18490.20380.18830.084*
C110.0620 (2)0.39801 (17)0.64874 (14)0.0503 (5)
H11A0.16930.41330.67930.075*
H11B0.01910.47420.66320.075*
H11C0.01970.33920.67910.075*
C120.1366 (2)0.23677 (15)0.50178 (13)0.0380 (4)
C130.1780 (2)0.17067 (15)0.56405 (13)0.0399 (4)
H130.17320.20250.63720.048*
C140.2284 (2)0.05421 (15)0.51881 (12)0.0363 (4)
C150.2678 (2)0.01956 (16)0.57923 (13)0.0389 (4)
H150.26090.00800.65280.047*
C160.3161 (2)0.13101 (15)0.53138 (12)0.0367 (4)
C170.3539 (2)0.21620 (16)0.59144 (13)0.0420 (4)
H17A0.47700.20390.59550.050*
H17B0.29910.19690.66320.050*
C180.2881 (2)0.35105 (16)0.53657 (13)0.0407 (4)
H18A0.16360.36580.53920.049*
H18B0.32050.40540.57310.049*
C190.3629 (2)0.37920 (15)0.42298 (13)0.0371 (4)
C200.4070 (2)0.49115 (16)0.37127 (13)0.0392 (4)
H200.38310.55590.40480.047*
C210.4883 (2)0.50919 (16)0.26757 (13)0.0388 (4)
C220.5414 (2)0.62236 (16)0.21068 (13)0.0431 (4)
H220.51340.69090.23950.052*
C230.6327 (2)0.63118 (16)0.11439 (14)0.0456 (4)
C240.6343 (3)0.84741 (18)0.08321 (18)0.0705 (6)
H24A0.51090.86550.09060.106*
H24B0.67710.91310.03000.106*
H24C0.67710.84040.14970.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0763 (10)0.0485 (8)0.0443 (7)0.0233 (7)0.0094 (6)0.0136 (6)
O20.0957 (11)0.0415 (7)0.0556 (8)0.0287 (7)0.0082 (7)0.0109 (6)
O30.0583 (8)0.0428 (7)0.0470 (7)0.0167 (6)0.0071 (6)0.0152 (6)
O40.0567 (8)0.0389 (7)0.0479 (7)0.0177 (6)0.0053 (6)0.0049 (5)
O50.0851 (13)0.1201 (16)0.1229 (16)0.0257 (12)0.0029 (11)0.0562 (13)
O60.1045 (15)0.1284 (17)0.1036 (14)0.0254 (13)0.0160 (11)0.0697 (13)
O70.1072 (13)0.0920 (12)0.0582 (9)0.0488 (11)0.0187 (9)0.0035 (8)
N10.0414 (8)0.0369 (7)0.0386 (7)0.0096 (6)0.0033 (6)0.0125 (6)
N20.0368 (7)0.0374 (7)0.0372 (7)0.0090 (6)0.0030 (6)0.0120 (6)
C10.0743 (14)0.0580 (12)0.0514 (11)0.0185 (11)0.0116 (10)0.0205 (10)
C20.0499 (11)0.0438 (10)0.0375 (9)0.0128 (8)0.0025 (8)0.0117 (8)
C30.0511 (10)0.0369 (9)0.0418 (9)0.0117 (8)0.0017 (8)0.0145 (7)
C40.0416 (9)0.0355 (9)0.0388 (9)0.0076 (7)0.0086 (7)0.0108 (7)
C50.0321 (8)0.0382 (9)0.0392 (9)0.0080 (7)0.0044 (7)0.0136 (7)
C60.0303 (8)0.0377 (9)0.0372 (8)0.0065 (7)0.0016 (6)0.0134 (7)
C70.0318 (8)0.0344 (8)0.0394 (9)0.0053 (7)0.0030 (7)0.0106 (7)
C80.0391 (9)0.0400 (9)0.0357 (8)0.0070 (7)0.0032 (7)0.0112 (7)
C90.0338 (9)0.0357 (9)0.0447 (9)0.0060 (7)0.0038 (7)0.0132 (7)
C100.0702 (13)0.0583 (12)0.0485 (11)0.0190 (10)0.0096 (10)0.0201 (9)
C110.0524 (11)0.0455 (10)0.0473 (10)0.0113 (9)0.0006 (8)0.0018 (8)
C120.0335 (9)0.0332 (9)0.0453 (9)0.0055 (7)0.0030 (7)0.0071 (7)
C130.0400 (9)0.0393 (9)0.0389 (9)0.0069 (7)0.0053 (7)0.0065 (7)
C140.0312 (8)0.0379 (9)0.0395 (9)0.0046 (7)0.0036 (7)0.0100 (7)
C150.0398 (9)0.0446 (10)0.0330 (8)0.0062 (7)0.0035 (7)0.0117 (7)
C160.0335 (8)0.0408 (9)0.0383 (9)0.0049 (7)0.0035 (7)0.0154 (7)
C170.0421 (10)0.0501 (10)0.0386 (9)0.0106 (8)0.0037 (7)0.0174 (8)
C180.0389 (9)0.0455 (10)0.0441 (9)0.0098 (8)0.0008 (7)0.0226 (8)
C190.0314 (8)0.0413 (9)0.0426 (9)0.0054 (7)0.0041 (7)0.0177 (7)
C200.0400 (9)0.0385 (9)0.0441 (9)0.0052 (7)0.0050 (7)0.0193 (7)
C210.0386 (9)0.0376 (9)0.0429 (9)0.0066 (7)0.0077 (7)0.0130 (7)
C220.0519 (11)0.0363 (9)0.0459 (10)0.0088 (8)0.0095 (8)0.0148 (8)
C230.0575 (11)0.0362 (9)0.0453 (10)0.0143 (8)0.0077 (8)0.0077 (8)
C240.1042 (18)0.0384 (11)0.0685 (14)0.0224 (11)0.0009 (13)0.0087 (10)
Geometric parameters (Å, º) top
O1—C21.356 (2)C8—C91.361 (2)
O1—C11.423 (2)C8—H80.9300
O2—C231.356 (2)C9—C121.429 (2)
O2—C241.421 (2)C10—H10A0.9600
O3—C91.366 (2)C10—H10B0.9600
O3—C101.426 (2)C10—H10C0.9600
O4—C121.3619 (19)C11—H11A0.9600
O4—C111.421 (2)C11—H11B0.9600
O5—H5B0.8412C11—H11C0.9600
O5—H5A0.8292C12—C131.362 (2)
O6—H6B0.8408C13—C141.414 (2)
O6—H6A0.8407C13—H130.9300
O7—H7B0.8516C14—C151.404 (2)
O7—H7A0.8460C15—C161.363 (2)
N1—C51.326 (2)C15—H150.9300
N1—C41.366 (2)C16—C171.501 (2)
N2—C61.331 (2)C17—C181.525 (2)
N2—C71.363 (2)C17—H17A0.9700
C1—H1A0.9600C17—H17B0.9700
C1—H1B0.9600C18—C191.503 (2)
C1—H1C0.9600C18—H18A0.9700
C2—C31.360 (2)C18—H18B0.9700
C2—C231.435 (2)C19—C201.364 (2)
C3—C41.413 (2)C20—C211.405 (2)
C3—H30.9300C20—H200.9300
C4—C211.417 (2)C21—C221.420 (2)
C5—C191.422 (2)C22—C231.358 (2)
C5—C61.480 (2)C22—H220.9300
C6—C161.419 (2)C24—H24A0.9600
C7—C81.415 (2)C24—H24B0.9600
C7—C141.419 (2)C24—H24C0.9600
C2—O1—C1117.33 (14)H11B—C11—H11C109.5
C23—O2—C24118.35 (16)O4—C12—C13125.46 (15)
C9—O3—C10117.31 (13)O4—C12—C9114.61 (15)
C12—O4—C11117.65 (14)C13—C12—C9119.93 (15)
H5B—O5—H5A99.6C12—C13—C14120.84 (15)
H6B—O6—H6A103.7C12—C13—H13119.6
H7B—O7—H7A108.5C14—C13—H13119.6
C5—N1—C4118.22 (14)C15—C14—C13123.32 (15)
C6—N2—C7118.19 (13)C15—C14—C7117.60 (15)
O1—C1—H1A109.5C13—C14—C7119.08 (15)
O1—C1—H1B109.5C16—C15—C14120.83 (15)
H1A—C1—H1B109.5C16—C15—H15119.6
O1—C1—H1C109.5C14—C15—H15119.6
H1A—C1—H1C109.5C15—C16—C6117.71 (15)
H1B—C1—H1C109.5C15—C16—C17123.46 (14)
O1—C2—C3126.20 (16)C6—C16—C17118.83 (14)
O1—C2—C23113.70 (15)C16—C17—C18110.44 (13)
C3—C2—C23120.09 (16)C16—C17—H17A109.6
C2—C3—C4120.61 (16)C18—C17—H17A109.6
C2—C3—H3119.7C16—C17—H17B109.6
C4—C3—H3119.7C18—C17—H17B109.6
N1—C4—C3118.87 (15)H17A—C17—H17B108.1
N1—C4—C21121.81 (15)C19—C18—C17109.89 (14)
C3—C4—C21119.31 (15)C19—C18—H18A109.7
N1—C5—C19123.50 (15)C17—C18—H18A109.7
N1—C5—C6118.32 (14)C19—C18—H18B109.7
C19—C5—C6118.18 (14)C17—C18—H18B109.7
N2—C6—C16123.63 (15)H18A—C18—H18B108.2
N2—C6—C5118.44 (14)C20—C19—C5117.95 (15)
C16—C6—C5117.93 (14)C20—C19—C18122.85 (15)
N2—C7—C8118.88 (14)C5—C19—C18119.19 (15)
N2—C7—C14121.93 (15)C19—C20—C21120.31 (16)
C8—C7—C14119.19 (15)C19—C20—H20119.8
C9—C8—C7120.56 (15)C21—C20—H20119.8
C9—C8—H8119.7C20—C21—C4117.83 (16)
C7—C8—H8119.7C20—C21—C22122.97 (16)
C8—C9—O3125.18 (15)C4—C21—C22119.14 (15)
C8—C9—C12120.36 (15)C23—C22—C21120.43 (16)
O3—C9—C12114.46 (14)C23—C22—H22119.8
O3—C10—H10A109.5C21—C22—H22119.8
O3—C10—H10B109.5O2—C23—C22125.85 (17)
H10A—C10—H10B109.5O2—C23—C2113.89 (15)
O3—C10—H10C109.5C22—C23—C2120.25 (16)
H10A—C10—H10C109.5O2—C24—H24A109.5
H10B—C10—H10C109.5O2—C24—H24B109.5
O4—C11—H11A109.5H24A—C24—H24B109.5
O4—C11—H11B109.5O2—C24—H24C109.5
H11A—C11—H11B109.5H24A—C24—H24C109.5
O4—C11—H11C109.5H24B—C24—H24C109.5
H11A—C11—H11C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O60.832.052.872 (2)169
O5—H5B···O7i0.842.082.877 (3)159
O6—H6B···N10.842.162.987 (3)167
O7—H7A···O1ii0.852.343.113 (2)152
O7—H7A···O2ii0.852.242.944 (2)140
O7—H7B···N20.852.122.938 (2)161
C18—H18A···O4iii0.972.423.282 (2)147
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x, y, z+1.
 

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