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The asymmetric unit of the title compound, C15H16N2O2, contains two mol­ecules and in each of the mol­ecules, the two aromatic rings, lying in two different planes, are bridged by a secondary amino group. This might be due to steric hindrance caused by the isopropyl group. Intra- and inter­molecular N—H...O hydrogen bonds link the mol­ecules, forming an infinite one-dimensional tape structure; they may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034131/hk2102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034131/hk2102Isup2.hkl
Contains datablock I

CCDC reference: 621364

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.051
  • wR factor = 0.141
  • Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C3B - C7B .. 5.54 su PLAT432_ALERT_2_C Short Inter X...Y Contact O9B .. C16B .. 2.94 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 50.00 A   3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local procedures.

2-(2-Isopropylanilino)pyridine-3-carboxylic acid top
Crystal data top
C15H16N2O2Dx = 1.231 Mg m3
Mr = 256.30Melting point = 441–443 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 22.242 (3) ÅCell parameters from 6707 reflections
b = 8.921 (1) Åθ = 1.0–27.5°
c = 14.367 (2) ŵ = 0.08 mm1
β = 104.07 (1)°T = 90 K
V = 2765.2 (6) Å3Rod, colorless
Z = 80.40 × 0.20 × 0.15 mm
F(000) = 1088
Data collection top
Nonius KappaCCD
diffractometer
6330 independent reflections
Radiation source: fine-focus sealed tube3912 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 1.9°
ω scans at fixed χ = 55°h = 2828
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 1111
Tmin = 0.968, Tmax = 0.988l = 1818
12239 measured reflections
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0776P)2]
where P = (Fo2 + 2Fc2)/3
6330 reflections(Δ/σ)max = 0.001
349 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.29 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
C2A0.15207 (7)0.21756 (18)0.48795 (11)0.0177 (4)
C3A0.15010 (7)0.30602 (18)0.56991 (11)0.0171 (4)
C4A0.14758 (8)0.45990 (19)0.55977 (12)0.0208 (4)
H4A0.14470.52100.61260.025*
C5A0.14927 (8)0.52592 (19)0.47326 (12)0.0231 (4)
H5A0.14750.63170.46560.028*
C6A0.15355 (8)0.43297 (18)0.39899 (12)0.0215 (4)
H6A0.15600.47800.34010.026*
C7A0.15146 (7)0.23523 (19)0.66397 (11)0.0190 (4)
C11A0.15841 (8)0.03126 (18)0.41624 (11)0.0187 (4)
C12A0.10632 (8)0.09367 (18)0.35331 (12)0.0203 (4)
C13A0.11667 (8)0.19322 (18)0.28401 (12)0.0225 (4)
H13A0.08210.23710.24030.027*
C14A0.17597 (8)0.22975 (18)0.27720 (12)0.0231 (4)
H14A0.18170.29890.22990.028*
C15A0.22673 (8)0.16552 (18)0.33927 (12)0.0232 (4)
H15A0.26750.18930.33440.028*
C16A0.21759 (8)0.06630 (18)0.40846 (12)0.0211 (4)
H16A0.25240.02170.45120.025*
C17A0.04136 (8)0.0562 (2)0.36204 (13)0.0271 (4)
H17A0.04240.04810.38790.033*
C18A0.02199 (9)0.1607 (2)0.43428 (14)0.0330 (5)
H18A0.02120.26440.41150.050*
H18B0.01940.13250.44080.050*
H18C0.05170.15200.49670.050*
C19A0.00715 (9)0.0593 (2)0.26596 (14)0.0393 (5)
H19A0.00700.00300.21930.059*
H19B0.04660.02030.27480.059*
H19C0.01290.16260.24230.059*
N1A0.15455 (6)0.28303 (15)0.40395 (9)0.0200 (3)
N10A0.15125 (6)0.06670 (15)0.49177 (10)0.0212 (3)
H10A0.14590.02520.54470.025*
O8A0.15063 (6)0.09942 (13)0.67621 (8)0.0247 (3)
O9A0.15407 (6)0.33463 (13)0.73272 (8)0.0287 (3)
H9A0.15420.29010.78430.043*
C2B0.33587 (7)0.21280 (18)0.29094 (12)0.0183 (4)
C3B0.32976 (7)0.30409 (18)0.36971 (12)0.0192 (4)
C4B0.31500 (8)0.45364 (19)0.35233 (12)0.0239 (4)
H4B0.31110.51690.40370.029*
C5B0.30581 (8)0.5121 (2)0.26052 (12)0.0254 (4)
H5B0.29660.61520.24800.031*
C6B0.31057 (8)0.41540 (19)0.18846 (12)0.0222 (4)
H6B0.30320.45450.12520.027*
C7B0.33879 (8)0.24165 (19)0.46756 (12)0.0217 (4)
C11B0.35540 (8)0.03994 (18)0.23240 (12)0.0189 (4)
C12B0.41013 (8)0.12069 (18)0.23552 (13)0.0224 (4)
C13B0.40868 (8)0.2267 (2)0.16415 (13)0.0266 (4)
H13B0.44510.28230.16440.032*
C14B0.35553 (8)0.25361 (19)0.09259 (12)0.0266 (4)
H14B0.35590.32640.04450.032*
C15B0.30206 (8)0.17451 (19)0.09140 (12)0.0244 (4)
H15B0.26550.19250.04250.029*
C16B0.30202 (8)0.06879 (18)0.16184 (12)0.0217 (4)
H16B0.26500.01550.16180.026*
C17B0.46777 (8)0.0946 (2)0.31622 (13)0.0291 (5)
H17B0.46830.01370.33440.035*
C18B0.46463 (9)0.1868 (2)0.40496 (14)0.0408 (5)
H18D0.42650.16220.42430.061*
H18E0.50060.16320.45760.061*
H18F0.46490.29380.38970.061*
C19B0.52826 (9)0.1276 (2)0.28812 (16)0.0398 (5)
H19D0.53120.23530.27650.060*
H19E0.56330.09660.34020.060*
H19F0.52920.07210.22960.060*
N1B0.32483 (6)0.26943 (15)0.20096 (9)0.0199 (3)
N10B0.35399 (6)0.06770 (15)0.30487 (10)0.0199 (3)
H10B0.36610.03710.36470.024*
O8B0.35764 (5)0.11428 (13)0.49036 (8)0.0243 (3)
O9B0.32383 (7)0.33796 (13)0.52777 (9)0.0339 (3)
H9B0.32810.29720.58170.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2A0.0187 (8)0.0192 (9)0.0159 (9)0.0003 (7)0.0054 (7)0.0015 (7)
C3A0.0201 (8)0.0182 (9)0.0124 (9)0.0002 (7)0.0030 (7)0.0004 (7)
C4A0.0254 (9)0.0213 (9)0.0157 (9)0.0011 (7)0.0053 (7)0.0037 (7)
C5A0.0328 (10)0.0170 (9)0.0185 (9)0.0004 (7)0.0041 (8)0.0010 (8)
C6A0.0302 (10)0.0189 (9)0.0152 (9)0.0014 (7)0.0051 (7)0.0029 (7)
C7A0.0221 (9)0.0188 (9)0.0162 (9)0.0006 (7)0.0047 (7)0.0022 (8)
C11A0.0310 (10)0.0140 (8)0.0119 (8)0.0012 (7)0.0070 (7)0.0026 (7)
C12A0.0265 (9)0.0171 (9)0.0179 (9)0.0000 (7)0.0066 (7)0.0022 (7)
C13A0.0314 (10)0.0189 (9)0.0163 (9)0.0037 (7)0.0044 (7)0.0006 (7)
C14A0.0381 (11)0.0173 (9)0.0163 (9)0.0012 (8)0.0111 (8)0.0014 (7)
C15A0.0301 (10)0.0202 (9)0.0217 (10)0.0018 (7)0.0110 (8)0.0024 (8)
C16A0.0250 (9)0.0194 (9)0.0185 (9)0.0018 (7)0.0045 (7)0.0019 (7)
C17A0.0267 (10)0.0257 (10)0.0284 (11)0.0017 (8)0.0057 (8)0.0030 (8)
C18A0.0328 (11)0.0369 (12)0.0322 (12)0.0010 (9)0.0136 (9)0.0006 (9)
C19A0.0325 (11)0.0467 (13)0.0359 (12)0.0053 (10)0.0028 (9)0.0037 (10)
N1A0.0270 (8)0.0202 (8)0.0137 (7)0.0010 (6)0.0065 (6)0.0014 (6)
N10A0.0354 (8)0.0159 (7)0.0144 (8)0.0008 (6)0.0099 (6)0.0015 (6)
O8A0.0384 (8)0.0205 (7)0.0169 (7)0.0027 (5)0.0102 (5)0.0005 (5)
O9A0.0553 (9)0.0210 (7)0.0113 (6)0.0010 (6)0.0109 (6)0.0002 (5)
C2B0.0193 (8)0.0195 (9)0.0165 (9)0.0011 (7)0.0052 (7)0.0010 (7)
C3B0.0244 (9)0.0208 (9)0.0131 (9)0.0000 (7)0.0061 (7)0.0010 (7)
C4B0.0331 (10)0.0223 (10)0.0185 (10)0.0012 (8)0.0107 (8)0.0022 (8)
C5B0.0364 (11)0.0206 (9)0.0209 (10)0.0057 (8)0.0100 (8)0.0016 (8)
C6B0.0281 (10)0.0233 (10)0.0159 (9)0.0021 (8)0.0067 (7)0.0043 (8)
C7B0.0270 (9)0.0198 (10)0.0189 (9)0.0028 (7)0.0069 (7)0.0025 (8)
C11B0.0294 (9)0.0160 (9)0.0137 (9)0.0016 (7)0.0096 (7)0.0010 (7)
C12B0.0264 (9)0.0187 (9)0.0237 (10)0.0021 (7)0.0091 (8)0.0013 (8)
C13B0.0315 (10)0.0223 (10)0.0293 (11)0.0006 (8)0.0139 (8)0.0031 (8)
C14B0.0397 (11)0.0219 (10)0.0212 (10)0.0046 (8)0.0134 (8)0.0052 (8)
C15B0.0347 (10)0.0220 (9)0.0165 (9)0.0050 (8)0.0063 (8)0.0001 (8)
C16B0.0294 (10)0.0174 (9)0.0198 (10)0.0001 (7)0.0090 (8)0.0029 (8)
C17B0.0277 (10)0.0291 (11)0.0304 (11)0.0024 (8)0.0070 (8)0.0038 (9)
C18B0.0386 (12)0.0481 (14)0.0323 (12)0.0040 (10)0.0024 (9)0.0042 (10)
C19B0.0306 (11)0.0464 (13)0.0427 (13)0.0006 (9)0.0094 (10)0.0054 (10)
N1B0.0244 (8)0.0204 (8)0.0155 (8)0.0021 (6)0.0058 (6)0.0016 (6)
N10B0.0307 (8)0.0175 (8)0.0109 (7)0.0028 (6)0.0042 (6)0.0009 (6)
O8B0.0358 (7)0.0208 (7)0.0162 (7)0.0016 (5)0.0065 (5)0.0005 (5)
O9B0.0657 (10)0.0242 (7)0.0161 (7)0.0075 (6)0.0185 (7)0.0020 (6)
Geometric parameters (Å, º) top
C2A—N10A1.347 (2)C2B—N1B1.354 (2)
C2A—N1A1.354 (2)C2B—N10B1.356 (2)
C2A—C3A1.427 (2)C2B—C3B1.427 (2)
C3A—C4A1.380 (2)C3B—C4B1.382 (2)
C3A—C7A1.485 (2)C3B—C7B1.480 (2)
C4A—C5A1.384 (2)C4B—C5B1.386 (2)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.373 (2)C5B—C6B1.371 (2)
C5A—H5A0.9500C5B—H5B0.9500
C6A—N1A1.339 (2)C6B—N1B1.342 (2)
C6A—H6A0.9500C6B—H6B0.9500
C7A—O8A1.2250 (19)C7B—O8B1.2277 (19)
C7A—O9A1.3181 (19)C7B—O9B1.3180 (19)
C11A—C16A1.384 (2)C11B—C16B1.385 (2)
C11A—C12A1.400 (2)C11B—C12B1.406 (2)
C11A—N10A1.432 (2)C11B—N10B1.422 (2)
C12A—C13A1.394 (2)C12B—C13B1.389 (2)
C12A—C17A1.517 (2)C12B—C17B1.523 (2)
C13A—C14A1.385 (2)C13B—C14B1.386 (2)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.382 (2)C14B—C15B1.379 (2)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.383 (2)C15B—C16B1.384 (2)
C15A—H15A0.9500C15B—H15B0.9500
C16A—H16A0.9500C16B—H16B0.9500
C17A—C19A1.532 (2)C17B—C19B1.524 (3)
C17A—C18A1.532 (3)C17B—C18B1.533 (3)
C17A—H17A1.0000C17B—H17B1.0000
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C19A—H19A0.9800C19B—H19D0.9800
C19A—H19B0.9800C19B—H19E0.9800
C19A—H19C0.9800C19B—H19F0.9800
N10A—H10A0.8800N10B—H10B0.8800
O9A—H9A0.8400O9B—H9B0.8400
N10A—C2A—N1A118.11 (14)N1B—C2B—N10B118.40 (14)
N10A—C2A—C3A121.02 (15)N1B—C2B—C3B120.94 (15)
N1A—C2A—C3A120.87 (15)N10B—C2B—C3B120.65 (14)
C4A—C3A—C2A118.13 (15)C4B—C3B—C2B118.14 (15)
C4A—C3A—C7A120.68 (15)C4B—C3B—C7B120.43 (15)
C2A—C3A—C7A121.18 (14)C2B—C3B—C7B121.43 (15)
C3A—C4A—C5A120.58 (16)C3B—C4B—C5B120.57 (16)
C3A—C4A—H4A119.7C3B—C4B—H4B119.7
C5A—C4A—H4A119.7C5B—C4B—H4B119.7
C6A—C5A—C4A117.58 (16)C6B—C5B—C4B117.47 (16)
C6A—C5A—H5A121.2C6B—C5B—H5B121.3
C4A—C5A—H5A121.2C4B—C5B—H5B121.3
N1A—C6A—C5A124.42 (16)N1B—C6B—C5B124.64 (16)
N1A—C6A—H6A117.8N1B—C6B—H6B117.7
C5A—C6A—H6A117.8C5B—C6B—H6B117.7
O8A—C7A—O9A123.86 (15)O8B—C7B—O9B123.53 (16)
O8A—C7A—C3A123.60 (15)O8B—C7B—C3B124.10 (15)
O9A—C7A—C3A112.53 (14)O9B—C7B—C3B112.37 (14)
C16A—C11A—C12A120.80 (16)C16B—C11B—C12B120.65 (16)
C16A—C11A—N10A118.84 (14)C16B—C11B—N10B119.58 (15)
C12A—C11A—N10A120.33 (15)C12B—C11B—N10B119.71 (15)
C13A—C12A—C11A117.39 (15)C13B—C12B—C11B117.42 (16)
C13A—C12A—C17A121.66 (15)C13B—C12B—C17B122.01 (16)
C11A—C12A—C17A120.94 (15)C11B—C12B—C17B120.54 (15)
C14A—C13A—C12A121.71 (16)C14B—C13B—C12B121.87 (17)
C14A—C13A—H13A119.1C14B—C13B—H13B119.1
C12A—C13A—H13A119.1C12B—C13B—H13B119.1
C15A—C14A—C13A119.98 (16)C15B—C14B—C13B119.86 (17)
C15A—C14A—H14A120.0C15B—C14B—H14B120.1
C13A—C14A—H14A120.0C13B—C14B—H14B120.1
C14A—C15A—C16A119.33 (16)C14B—C15B—C16B119.57 (16)
C14A—C15A—H15A120.3C14B—C15B—H15B120.2
C16A—C15A—H15A120.3C16B—C15B—H15B120.2
C15A—C16A—C11A120.78 (16)C15B—C16B—C11B120.61 (16)
C15A—C16A—H16A119.6C15B—C16B—H16B119.7
C11A—C16A—H16A119.6C11B—C16B—H16B119.7
C12A—C17A—C19A113.44 (16)C12B—C17B—C19B113.75 (16)
C12A—C17A—C18A110.63 (14)C12B—C17B—C18B110.56 (15)
C19A—C17A—C18A110.31 (15)C19B—C17B—C18B109.78 (16)
C12A—C17A—H17A107.4C12B—C17B—H17B107.5
C19A—C17A—H17A107.4C19B—C17B—H17B107.5
C18A—C17A—H17A107.4C18B—C17B—H17B107.5
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C17A—C19A—H19A109.5C17B—C19B—H19D109.5
C17A—C19A—H19B109.5C17B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C17A—C19A—H19C109.5C17B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C6A—N1A—C2A118.33 (14)C6B—N1B—C2B118.17 (14)
C2A—N10A—C11A125.01 (14)C2B—N10B—C11B126.51 (14)
C2A—N10A—H10A117.5C2B—N10B—H10B116.7
C11A—N10A—H10A117.5C11B—N10B—H10B116.7
C7A—O9A—H9A109.5C7B—O9B—H9B109.5
N10A—C2A—C3A—C4A176.44 (15)N1B—C2B—C3B—C4B2.9 (2)
N1A—C2A—C3A—C4A3.3 (2)N10B—C2B—C3B—C4B175.94 (15)
N10A—C2A—C3A—C7A4.3 (2)N1B—C2B—C3B—C7B177.05 (14)
N1A—C2A—C3A—C7A176.03 (14)N10B—C2B—C3B—C7B4.1 (2)
C2A—C3A—C4A—C5A2.4 (2)C2B—C3B—C4B—C5B0.7 (2)
C7A—C3A—C4A—C5A176.94 (15)C7B—C3B—C4B—C5B179.26 (15)
C3A—C4A—C5A—C6A0.1 (2)C3B—C4B—C5B—C6B1.4 (3)
C4A—C5A—C6A—N1A1.8 (3)C4B—C5B—C6B—N1B1.6 (3)
C4A—C3A—C7A—O8A176.29 (16)C4B—C3B—C7B—O8B172.78 (16)
C2A—C3A—C7A—O8A4.4 (2)C2B—C3B—C7B—O8B7.3 (3)
C4A—C3A—C7A—O9A4.1 (2)C4B—C3B—C7B—O9B7.7 (2)
C2A—C3A—C7A—O9A175.13 (14)C2B—C3B—C7B—O9B172.20 (14)
C16A—C11A—C12A—C13A0.8 (2)C16B—C11B—C12B—C13B1.6 (2)
N10A—C11A—C12A—C13A177.27 (14)N10B—C11B—C12B—C13B178.70 (15)
C16A—C11A—C12A—C17A179.61 (15)C16B—C11B—C12B—C17B176.72 (16)
N10A—C11A—C12A—C17A1.5 (2)N10B—C11B—C12B—C17B0.4 (2)
C11A—C12A—C13A—C14A0.1 (3)C11B—C12B—C13B—C14B0.4 (3)
C17A—C12A—C13A—C14A178.70 (15)C17B—C12B—C13B—C14B177.83 (16)
C12A—C13A—C14A—C15A0.8 (3)C12B—C13B—C14B—C15B0.3 (3)
C13A—C14A—C15A—C16A0.7 (3)C13B—C14B—C15B—C16B0.0 (3)
C14A—C15A—C16A—C11A0.2 (3)C14B—C15B—C16B—C11B1.1 (3)
C12A—C11A—C16A—C15A1.0 (3)C12B—C11B—C16B—C15B1.9 (2)
N10A—C11A—C16A—C15A177.16 (15)N10B—C11B—C16B—C15B179.09 (15)
C13A—C12A—C17A—C19A32.1 (2)C13B—C12B—C17B—C19B29.4 (2)
C11A—C12A—C17A—C19A149.15 (17)C11B—C12B—C17B—C19B152.44 (16)
C13A—C12A—C17A—C18A92.4 (2)C13B—C12B—C17B—C18B94.7 (2)
C11A—C12A—C17A—C18A86.3 (2)C11B—C12B—C17B—C18B83.5 (2)
C5A—C6A—N1A—C2A1.0 (2)C5B—C6B—N1B—C2B0.6 (2)
N10A—C2A—N1A—C6A178.08 (14)N10B—C2B—N1B—C6B176.03 (14)
C3A—C2A—N1A—C6A1.6 (2)C3B—C2B—N1B—C6B2.8 (2)
N1A—C2A—N10A—C11A6.0 (2)N1B—C2B—N10B—C11B8.6 (2)
C3A—C2A—N10A—C11A174.35 (14)C3B—C2B—N10B—C11B172.55 (15)
C16A—C11A—N10A—C2A83.8 (2)C16B—C11B—N10B—C2B55.5 (2)
C12A—C11A—N10A—C2A98.0 (2)C12B—C11B—N10B—C2B127.29 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10A—H10A···O8A0.881.982.6694 (18)134
N10B—H10B···O8B0.881.982.6788 (18)135
O9A—H9A···N1Ai0.841.842.6723 (18)173
O9B—H9B···N1Bi0.841.832.6614 (18)169
Symmetry code: (i) x, y+1/2, z+1/2.
 

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