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In the title structure, C19H14N4O4, there are two crystallographically independent mol­ecules in the asymmetric unit. The nitro groups are coplanar with the attached benzene rings. The crystal structure is stabilized by weak inter­molecular C—H...O and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048112/sj2165sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048112/sj2165Isup2.hkl
Contains datablock I

CCDC reference: 630479

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.086
  • wR factor = 0.250
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: H.K. Fun is supervisor of Shea-Lin Ng whereas Muhammad I. Saleh is supervisor of Adassalam Abdelhafiz Tameem, Abdulssalam Salhin, Bahruddin Saad and Ismail Ab. Rahman in this collaborative publication. School of Chemical Sciences, Universiti Sains Malaysia is involved in the extraction and synthesis of the title compound and X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia is involved in the structure determination. All parties are involved in writing up the manuscript.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Benzophenone-2,4-dinitrophenylhydrazone top
Crystal data top
C19H14N4O4F(000) = 1504
Mr = 362.34Dx = 1.416 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2745 reflections
a = 13.6764 (6) Åθ = 1.1–25.0°
b = 6.9852 (3) ŵ = 0.10 mm1
c = 37.9306 (18) ÅT = 297 K
β = 110.253 (3)°Plate, light_orange
V = 3399.6 (3) Å30.36 × 0.29 × 0.12 mm
Z = 8
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
6003 independent reflections
Radiation source: fine-focus sealed tube2866 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 1.1°
ω scansh = 1616
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 88
Tmin = 0.964, Tmax = 0.988l = 4544
35803 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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.250H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.1037P)2 + 1.1324P]
where P = (Fo2 + 2Fc2)/3
6003 reflections(Δ/σ)max < 0.001
495 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.27 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
O1A0.0077 (2)0.0655 (5)0.59410 (9)0.0608 (9)
O2A0.1209 (2)0.0375 (5)0.62153 (9)0.0671 (10)
O3A0.0309 (3)0.1737 (6)0.74766 (10)0.0852 (13)
O4A0.1296 (3)0.2227 (6)0.78133 (10)0.0882 (13)
N1A0.2973 (3)0.0472 (5)0.63932 (10)0.0457 (9)
N2A0.1913 (3)0.0260 (5)0.63201 (11)0.0462 (10)
N3A0.0304 (3)0.0310 (5)0.62228 (11)0.0487 (10)
N4A0.0623 (4)0.1761 (6)0.75165 (12)0.0612 (11)
C1A0.5021 (4)0.1676 (6)0.65506 (13)0.0515 (12)
H1A0.47410.18310.67400.062*
C2A0.6080 (4)0.1940 (7)0.66303 (16)0.0627 (14)
H2A0.65050.22810.68720.075*
C3A0.6504 (4)0.1699 (7)0.63527 (19)0.0714 (16)
H3A0.72160.18580.64060.086*
C4A0.5871 (4)0.1228 (7)0.59994 (18)0.0662 (15)
H4A0.61530.10830.58100.079*
C5A0.4809 (4)0.0960 (7)0.59179 (14)0.0577 (13)
H5A0.43860.06260.56760.069*
C6A0.4380 (3)0.1186 (6)0.61947 (13)0.0445 (11)
C7A0.3248 (3)0.0834 (6)0.61092 (13)0.0442 (11)
C8A0.2525 (3)0.0875 (7)0.57119 (12)0.0452 (11)
C9A0.2229 (4)0.2593 (8)0.55305 (14)0.0640 (14)
H9A0.24890.37320.56550.077*
C10A0.1541 (4)0.2636 (10)0.51616 (16)0.0826 (17)
H10A0.13210.38040.50430.099*
C11A0.1190 (4)0.0982 (10)0.49741 (16)0.0754 (16)
H11A0.07430.10190.47250.090*
C12A0.1491 (4)0.0736 (9)0.51486 (16)0.0732 (16)
H12A0.12520.18720.50200.088*
C13A0.2149 (4)0.0776 (7)0.55157 (15)0.0655 (14)
H13A0.23460.19510.56350.079*
C14A0.1579 (3)0.0209 (6)0.66027 (12)0.0409 (11)
C15A0.0513 (3)0.0220 (6)0.65716 (12)0.0425 (11)
C16A0.0205 (3)0.0719 (6)0.68696 (13)0.0476 (12)
H16A0.04970.07080.68420.057*
C17A0.0936 (3)0.1227 (6)0.72036 (12)0.0459 (11)
C18A0.1995 (3)0.1237 (7)0.72493 (13)0.0530 (12)
H18A0.24900.15880.74780.064*
C19A0.2298 (3)0.0726 (6)0.69541 (12)0.0498 (12)
H19A0.30040.07220.69880.060*
O2B0.3749 (3)0.3936 (5)0.62378 (9)0.0692 (10)
O3B0.4694 (3)0.1804 (6)0.74998 (10)0.0868 (13)
O4B0.6300 (3)0.1241 (6)0.78269 (10)0.0847 (12)
N1B0.7906 (3)0.3905 (5)0.63908 (10)0.0464 (9)
N2B0.6860 (3)0.3689 (6)0.63202 (12)0.0487 (10)
N3B0.4642 (3)0.3754 (5)0.62334 (11)0.0488 (10)
N4B0.5618 (4)0.1719 (6)0.75331 (12)0.0600 (11)
C1B0.9944 (3)0.5229 (6)0.65585 (13)0.0494 (12)
H1B0.96430.55040.67380.059*
C2B1.1009 (4)0.5427 (7)0.66461 (14)0.0607 (14)
H2B1.14220.58280.68850.073*
C3B1.1461 (4)0.5033 (7)0.63820 (17)0.0655 (15)
H3B1.21790.51430.64450.079*
C4B1.0865 (4)0.4486 (8)0.60304 (17)0.0691 (15)
H4B1.11730.42390.58520.083*
C5B0.9791 (4)0.4294 (7)0.59365 (13)0.0552 (13)
H5B0.93820.39440.56940.066*
C6B0.9328 (3)0.4623 (6)0.62039 (12)0.0442 (11)
C7B0.8198 (3)0.4309 (6)0.61091 (13)0.0442 (11)
C8B0.7485 (3)0.4391 (7)0.57110 (13)0.0502 (12)
C13B0.7375 (4)0.6045 (8)0.55033 (15)0.0634 (14)
H13B0.77450.71390.56120.076*
C12B0.6710 (5)0.6074 (10)0.51316 (17)0.0823 (18)
H12B0.66320.71950.49920.099*
C11B0.6169 (4)0.4462 (12)0.49681 (17)0.087 (2)
H11B0.57260.44920.47190.104*
C10B0.6280 (4)0.2828 (11)0.51700 (16)0.090 (2)
H10B0.59150.17340.50590.108*
C9B0.6938 (4)0.2785 (8)0.55419 (14)0.0683 (15)
H9B0.70120.16570.56790.082*
C14B0.6536 (3)0.3218 (6)0.66095 (12)0.0396 (11)
C15B0.5462 (3)0.3243 (6)0.65786 (12)0.0398 (11)
C16B0.5180 (3)0.2789 (6)0.68813 (12)0.0444 (11)
H16B0.44820.28360.68600.053*
C17B0.5916 (3)0.2270 (6)0.72137 (12)0.0439 (11)
C18B0.6970 (3)0.2192 (6)0.72522 (13)0.0491 (12)
H18B0.74670.18110.74780.059*
C19B0.7261 (3)0.2676 (6)0.69568 (12)0.0476 (12)
H19B0.79650.26480.69860.057*
O1B0.4854 (2)0.3993 (5)0.59473 (9)0.0642 (10)
H2C0.148 (4)0.067 (7)0.6083 (13)0.073 (16)*
H2D0.640 (4)0.386 (7)0.6109 (13)0.065 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.048 (2)0.087 (3)0.046 (2)0.0039 (17)0.0152 (17)0.0057 (18)
O2A0.035 (2)0.089 (3)0.075 (2)0.0021 (17)0.0177 (18)0.0147 (19)
O3A0.051 (2)0.143 (4)0.071 (3)0.014 (2)0.033 (2)0.010 (2)
O4A0.065 (3)0.149 (4)0.050 (2)0.008 (2)0.019 (2)0.019 (2)
N1A0.036 (2)0.055 (2)0.051 (2)0.0035 (17)0.0209 (19)0.0009 (19)
N2A0.036 (2)0.061 (3)0.044 (3)0.0005 (18)0.017 (2)0.004 (2)
N3A0.040 (3)0.050 (2)0.055 (3)0.0066 (18)0.016 (2)0.002 (2)
N4A0.055 (3)0.086 (3)0.048 (3)0.014 (2)0.026 (2)0.002 (2)
C1A0.050 (3)0.055 (3)0.051 (3)0.003 (2)0.019 (3)0.007 (2)
C2A0.040 (3)0.058 (3)0.080 (4)0.008 (2)0.007 (3)0.001 (3)
C3A0.037 (3)0.066 (4)0.116 (5)0.001 (3)0.034 (4)0.010 (3)
C4A0.062 (4)0.059 (3)0.096 (5)0.003 (3)0.051 (4)0.001 (3)
C5A0.042 (3)0.067 (3)0.070 (4)0.006 (2)0.028 (3)0.003 (3)
C6A0.043 (3)0.047 (3)0.047 (3)0.005 (2)0.019 (2)0.005 (2)
C7A0.039 (3)0.051 (3)0.049 (3)0.003 (2)0.024 (2)0.001 (2)
C8A0.035 (3)0.061 (3)0.043 (3)0.000 (2)0.018 (2)0.005 (3)
C9A0.062 (3)0.068 (4)0.059 (3)0.004 (3)0.017 (3)0.004 (3)
C10A0.081 (4)0.095 (5)0.064 (4)0.005 (4)0.015 (3)0.021 (4)
C11A0.063 (4)0.104 (5)0.053 (3)0.013 (4)0.012 (3)0.006 (4)
C12A0.067 (4)0.079 (4)0.070 (4)0.020 (3)0.020 (3)0.021 (3)
C13A0.063 (3)0.061 (4)0.067 (4)0.009 (3)0.016 (3)0.012 (3)
C14A0.040 (3)0.048 (3)0.038 (3)0.004 (2)0.017 (2)0.003 (2)
C15A0.036 (3)0.047 (3)0.042 (3)0.002 (2)0.010 (2)0.001 (2)
C16A0.042 (3)0.055 (3)0.050 (3)0.009 (2)0.020 (2)0.006 (2)
C17A0.041 (3)0.059 (3)0.043 (3)0.008 (2)0.020 (2)0.008 (2)
C18A0.042 (3)0.069 (3)0.044 (3)0.007 (2)0.009 (2)0.005 (2)
C19A0.038 (3)0.067 (3)0.048 (3)0.002 (2)0.020 (2)0.001 (2)
O2B0.037 (2)0.094 (3)0.075 (2)0.0068 (18)0.0165 (18)0.0112 (19)
O3B0.054 (3)0.144 (4)0.073 (3)0.011 (2)0.035 (2)0.013 (2)
O4B0.069 (3)0.131 (3)0.051 (2)0.013 (2)0.016 (2)0.019 (2)
N1B0.031 (2)0.055 (2)0.053 (3)0.0040 (17)0.0157 (18)0.0013 (19)
N2B0.038 (3)0.066 (3)0.044 (3)0.0016 (19)0.016 (2)0.003 (2)
N3B0.044 (3)0.048 (2)0.049 (3)0.0021 (18)0.010 (2)0.0048 (19)
N4B0.055 (3)0.079 (3)0.051 (3)0.010 (2)0.024 (2)0.000 (2)
C1B0.049 (3)0.046 (3)0.055 (3)0.005 (2)0.020 (3)0.001 (2)
C2B0.044 (3)0.063 (3)0.063 (3)0.006 (2)0.003 (3)0.010 (3)
C3B0.043 (3)0.063 (4)0.095 (5)0.003 (2)0.029 (3)0.007 (3)
C4B0.057 (4)0.078 (4)0.087 (4)0.010 (3)0.042 (3)0.003 (3)
C5B0.046 (3)0.071 (3)0.052 (3)0.005 (2)0.020 (2)0.004 (3)
C6B0.039 (3)0.050 (3)0.050 (3)0.005 (2)0.022 (2)0.001 (2)
C7B0.041 (3)0.046 (3)0.049 (3)0.002 (2)0.021 (2)0.002 (2)
C8B0.039 (3)0.069 (4)0.046 (3)0.003 (2)0.019 (2)0.003 (3)
C13B0.046 (3)0.080 (4)0.066 (4)0.009 (3)0.021 (3)0.018 (3)
C12B0.065 (4)0.114 (5)0.072 (4)0.018 (4)0.030 (4)0.028 (4)
C11B0.051 (4)0.156 (7)0.050 (4)0.009 (4)0.013 (3)0.017 (4)
C10B0.066 (4)0.150 (6)0.050 (4)0.023 (4)0.016 (3)0.019 (4)
C9B0.066 (4)0.088 (4)0.053 (3)0.009 (3)0.025 (3)0.002 (3)
C14B0.037 (3)0.040 (3)0.045 (3)0.0011 (19)0.018 (2)0.003 (2)
C15B0.037 (3)0.043 (3)0.040 (3)0.0010 (19)0.014 (2)0.003 (2)
C16B0.035 (3)0.051 (3)0.049 (3)0.001 (2)0.017 (2)0.003 (2)
C17B0.047 (3)0.048 (3)0.041 (3)0.007 (2)0.022 (2)0.003 (2)
C18B0.036 (3)0.065 (3)0.045 (3)0.002 (2)0.013 (2)0.000 (2)
C19B0.032 (2)0.067 (3)0.044 (3)0.001 (2)0.013 (2)0.001 (2)
O1B0.053 (2)0.093 (3)0.047 (2)0.0082 (18)0.0166 (17)0.0179 (19)
Geometric parameters (Å, º) top
O1A—N3A1.236 (4)O2B—N3B1.234 (4)
O2A—N3A1.229 (4)O3B—N4B1.227 (5)
O3A—N4A1.231 (5)O4B—N4B1.226 (5)
O4A—N4A1.226 (5)N1B—C7B1.295 (5)
N1A—C7A1.283 (5)N1B—N2B1.369 (5)
N1A—N2A1.387 (5)N2B—C14B1.359 (5)
N2A—C14A1.343 (5)N2B—H2D0.84 (5)
N2A—H2C0.93 (5)N3B—O1B1.227 (4)
N3A—C15A1.453 (5)N3B—C15B1.443 (5)
N4A—C17A1.443 (5)N4B—C17B1.457 (5)
C1A—C6A1.374 (6)C1B—C6B1.383 (6)
C1A—C2A1.386 (6)C1B—C2B1.384 (6)
C1A—H1A0.9300C1B—H1B0.9300
C2A—C3A1.377 (7)C2B—C3B1.374 (6)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.360 (7)C3B—C4B1.355 (7)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.390 (6)C4B—C5B1.393 (6)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.378 (6)C5B—C6B1.388 (6)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.488 (6)C6B—C7B1.476 (6)
C7A—C8A1.489 (6)C7B—C8B1.488 (6)
C8A—C13A1.373 (6)C8B—C13B1.377 (6)
C8A—C9A1.373 (6)C8B—C9B1.377 (7)
C9A—C10A1.390 (7)C13B—C12B1.388 (7)
C9A—H9A0.9300C13B—H13B0.9300
C10A—C11A1.354 (8)C12B—C11B1.372 (8)
C10A—H10A0.9300C12B—H12B0.9300
C11A—C12A1.364 (7)C11B—C10B1.353 (8)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.372 (7)C10B—C9B1.386 (7)
C12A—H12A0.9300C10B—H10B0.9300
C13A—H13A0.9300C9B—H9B0.9300
C14A—C19A1.402 (6)C14B—C19B1.400 (6)
C14A—C15A1.421 (6)C14B—C15B1.433 (5)
C15A—C16A1.381 (5)C15B—C16B1.368 (5)
C16A—C17A1.361 (6)C16B—C17B1.362 (6)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.398 (6)C17B—C18B1.399 (5)
C18A—C19A1.369 (6)C18B—C19B1.356 (5)
C18A—H18A0.9300C18B—H18B0.9300
C19A—H19A0.9300C19B—H19B0.9300
C7A—N1A—N2A116.3 (4)C7B—N1B—N2B117.5 (4)
C14A—N2A—N1A119.2 (4)C14B—N2B—N1B118.7 (4)
C14A—N2A—H2C125 (3)C14B—N2B—H2D118 (3)
N1A—N2A—H2C115 (3)N1B—N2B—H2D124 (3)
O2A—N3A—O1A121.7 (4)O1B—N3B—O2B122.4 (4)
O2A—N3A—C15A118.8 (4)O1B—N3B—C15B119.3 (4)
O1A—N3A—C15A119.5 (4)O2B—N3B—C15B118.3 (4)
O4A—N4A—O3A122.2 (4)O4B—N4B—O3B122.6 (4)
O4A—N4A—C17A118.8 (4)O4B—N4B—C17B119.0 (4)
O3A—N4A—C17A119.0 (4)O3B—N4B—C17B118.4 (4)
C6A—C1A—C2A120.7 (5)C6B—C1B—C2B120.1 (5)
C6A—C1A—H1A119.6C6B—C1B—H1B120.0
C2A—C1A—H1A119.6C2B—C1B—H1B120.0
C3A—C2A—C1A120.1 (5)C3B—C2B—C1B120.4 (5)
C3A—C2A—H2A119.9C3B—C2B—H2B119.8
C1A—C2A—H2A119.9C1B—C2B—H2B119.8
C4A—C3A—C2A119.4 (5)C4B—C3B—C2B120.3 (5)
C4A—C3A—H3A120.3C4B—C3B—H3B119.8
C2A—C3A—H3A120.3C2B—C3B—H3B119.8
C3A—C4A—C5A120.7 (5)C3B—C4B—C5B120.0 (5)
C3A—C4A—H4A119.6C3B—C4B—H4B120.0
C5A—C4A—H4A119.6C5B—C4B—H4B120.0
C6A—C5A—C4A120.3 (5)C6B—C5B—C4B120.3 (5)
C6A—C5A—H5A119.9C6B—C5B—H5B119.8
C4A—C5A—H5A119.9C4B—C5B—H5B119.8
C1A—C6A—C5A118.8 (4)C1B—C6B—C5B118.8 (4)
C1A—C6A—C7A121.1 (4)C1B—C6B—C7B121.1 (4)
C5A—C6A—C7A120.0 (4)C5B—C6B—C7B120.1 (4)
N1A—C7A—C6A115.8 (4)N1B—C7B—C6B115.3 (4)
N1A—C7A—C8A124.7 (4)N1B—C7B—C8B124.3 (4)
C6A—C7A—C8A119.6 (4)C6B—C7B—C8B120.3 (4)
C13A—C8A—C9A118.2 (5)C13B—C8B—C9B118.9 (5)
C13A—C8A—C7A121.7 (4)C13B—C8B—C7B121.1 (5)
C9A—C8A—C7A120.1 (4)C9B—C8B—C7B120.1 (5)
C8A—C9A—C10A120.2 (5)C8B—C13B—C12B119.8 (5)
C8A—C9A—H9A119.9C8B—C13B—H13B120.1
C10A—C9A—H9A119.9C12B—C13B—H13B120.1
C11A—C10A—C9A120.3 (6)C11B—C12B—C13B120.6 (6)
C11A—C10A—H10A119.9C11B—C12B—H12B119.7
C9A—C10A—H10A119.9C13B—C12B—H12B119.7
C10A—C11A—C12A120.2 (5)C10B—C11B—C12B119.9 (6)
C10A—C11A—H11A119.9C10B—C11B—H11B120.0
C12A—C11A—H11A119.9C12B—C11B—H11B120.0
C11A—C12A—C13A119.5 (5)C11B—C10B—C9B120.0 (6)
C11A—C12A—H12A120.3C11B—C10B—H10B120.0
C13A—C12A—H12A120.3C9B—C10B—H10B120.0
C12A—C13A—C8A121.6 (5)C8B—C9B—C10B120.8 (6)
C12A—C13A—H13A119.2C8B—C9B—H9B119.6
C8A—C13A—H13A119.2C10B—C9B—H9B119.6
N2A—C14A—C19A120.1 (4)N2B—C14B—C19B120.1 (4)
N2A—C14A—C15A123.9 (4)N2B—C14B—C15B122.9 (4)
C19A—C14A—C15A116.0 (4)C19B—C14B—C15B117.0 (4)
C16A—C15A—C14A121.9 (4)C16B—C15B—C14B120.4 (4)
C16A—C15A—N3A116.9 (4)C16B—C15B—N3B117.6 (4)
C14A—C15A—N3A121.2 (4)C14B—C15B—N3B122.0 (4)
C17A—C16A—C15A119.6 (4)C17B—C16B—C15B120.4 (4)
C17A—C16A—H16A120.2C17B—C16B—H16B119.8
C15A—C16A—H16A120.2C15B—C16B—H16B119.8
C16A—C17A—C18A120.8 (4)C16B—C17B—C18B120.7 (4)
C16A—C17A—N4A120.2 (4)C16B—C17B—N4B120.7 (4)
C18A—C17A—N4A119.1 (4)C18B—C17B—N4B118.5 (4)
C19A—C18A—C17A119.4 (4)C19B—C18B—C17B119.4 (4)
C19A—C18A—H18A120.3C19B—C18B—H18B120.3
C17A—C18A—H18A120.3C17B—C18B—H18B120.3
C18A—C19A—C14A122.3 (4)C18B—C19B—C14B122.0 (4)
C18A—C19A—H19A118.9C18B—C19B—H19B119.0
C14A—C19A—H19A118.9C14B—C19B—H19B119.0
C7A—N1A—N2A—C14A176.9 (4)C7B—N1B—N2B—C14B178.4 (4)
C6A—C1A—C2A—C3A0.5 (7)C6B—C1B—C2B—C3B0.3 (7)
C1A—C2A—C3A—C4A0.9 (7)C1B—C2B—C3B—C4B1.4 (7)
C2A—C3A—C4A—C5A1.0 (8)C2B—C3B—C4B—C5B0.9 (8)
C3A—C4A—C5A—C6A0.6 (7)C3B—C4B—C5B—C6B1.3 (7)
C2A—C1A—C6A—C5A0.1 (7)C2B—C1B—C6B—C5B2.5 (6)
C2A—C1A—C6A—C7A177.9 (4)C2B—C1B—C6B—C7B177.0 (4)
C4A—C5A—C6A—C1A0.1 (7)C4B—C5B—C6B—C1B3.0 (7)
C4A—C5A—C6A—C7A178.0 (4)C4B—C5B—C6B—C7B176.5 (4)
N2A—N1A—C7A—C6A176.1 (3)N2B—N1B—C7B—C6B177.0 (3)
N2A—N1A—C7A—C8A5.3 (6)N2B—N1B—C7B—C8B5.4 (6)
C1A—C6A—C7A—N1A19.3 (6)C1B—C6B—C7B—N1B25.7 (6)
C5A—C6A—C7A—N1A158.5 (4)C5B—C6B—C7B—N1B153.8 (4)
C1A—C6A—C7A—C8A162.1 (4)C1B—C6B—C7B—C8B156.7 (4)
C5A—C6A—C7A—C8A20.1 (6)C5B—C6B—C7B—C8B23.9 (6)
N1A—C7A—C8A—C13A75.7 (6)N1B—C7B—C8B—C13B120.6 (5)
C6A—C7A—C8A—C13A102.8 (5)C6B—C7B—C8B—C13B61.9 (6)
N1A—C7A—C8A—C9A105.2 (5)N1B—C7B—C8B—C9B60.8 (6)
C6A—C7A—C8A—C9A76.3 (5)C6B—C7B—C8B—C9B116.6 (5)
C13A—C8A—C9A—C10A1.9 (7)C9B—C8B—C13B—C12B0.9 (7)
C7A—C8A—C9A—C10A179.0 (4)C7B—C8B—C13B—C12B179.4 (4)
C8A—C9A—C10A—C11A2.5 (8)C8B—C13B—C12B—C11B0.6 (8)
C9A—C10A—C11A—C12A1.5 (9)C13B—C12B—C11B—C10B0.1 (9)
C10A—C11A—C12A—C13A0.2 (8)C12B—C11B—C10B—C9B0.2 (9)
C11A—C12A—C13A—C8A0.8 (8)C13B—C8B—C9B—C10B0.6 (7)
C9A—C8A—C13A—C12A0.3 (7)C7B—C8B—C9B—C10B179.2 (5)
C7A—C8A—C13A—C12A179.4 (4)C11B—C10B—C9B—C8B0.1 (8)
N1A—N2A—C14A—C19A8.5 (6)N1B—N2B—C14B—C19B9.8 (6)
N1A—N2A—C14A—C15A171.5 (4)N1B—N2B—C14B—C15B170.2 (4)
N2A—C14A—C15A—C16A179.7 (4)N2B—C14B—C15B—C16B178.8 (4)
C19A—C14A—C15A—C16A0.3 (6)C19B—C14B—C15B—C16B1.2 (6)
N2A—C14A—C15A—N3A0.6 (6)N2B—C14B—C15B—N3B0.7 (6)
C19A—C14A—C15A—N3A179.3 (4)C19B—C14B—C15B—N3B179.2 (4)
O2A—N3A—C15A—C16A3.4 (6)O1B—N3B—C15B—C16B173.2 (4)
O1A—N3A—C15A—C16A175.6 (4)O2B—N3B—C15B—C16B6.9 (6)
O2A—N3A—C15A—C14A176.3 (4)O1B—N3B—C15B—C14B7.3 (6)
O1A—N3A—C15A—C14A4.8 (6)O2B—N3B—C15B—C14B172.7 (4)
C14A—C15A—C16A—C17A0.3 (6)C14B—C15B—C16B—C17B1.3 (6)
N3A—C15A—C16A—C17A180.0 (4)N3B—C15B—C16B—C17B179.1 (4)
C15A—C16A—C17A—C18A0.4 (7)C15B—C16B—C17B—C18B0.0 (6)
C15A—C16A—C17A—N4A179.7 (4)C15B—C16B—C17B—N4B177.8 (4)
O4A—N4A—C17A—C16A179.5 (4)O4B—N4B—C17B—C16B179.3 (4)
O3A—N4A—C17A—C16A0.5 (6)O3B—N4B—C17B—C16B2.7 (6)
O4A—N4A—C17A—C18A0.7 (6)O4B—N4B—C17B—C18B1.4 (6)
O3A—N4A—C17A—C18A179.4 (4)O3B—N4B—C17B—C18B179.4 (4)
C16A—C17A—C18A—C19A0.1 (7)C16B—C17B—C18B—C19B1.3 (7)
N4A—C17A—C18A—C19A179.8 (4)N4B—C17B—C18B—C19B179.2 (4)
C17A—C18A—C19A—C14A0.7 (7)C17B—C18B—C19B—C14B1.4 (7)
N2A—C14A—C19A—C18A179.2 (4)N2B—C14B—C19B—C18B179.8 (4)
C15A—C14A—C19A—C18A0.8 (6)C15B—C14B—C19B—C18B0.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2C···O1A0.93 (5)2.01 (6)2.616 (5)121 (4)
N2B—H2D···O1B0.84 (5)1.99 (6)2.624 (5)132 (5)
C19A—H19A···O3B0.932.563.301 (6)136
C19B—H19B···O3Ai0.932.533.290 (6)139
C11B—H11B···O1Bii0.932.603.437 (7)150
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1.
 

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