Benzophenone 2,4-dinitro­phenyl­hydrazone

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.

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

No syntax errors found



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

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Computing details

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

Crystal data

C19H14N4O4	F(000) = 1504
Mr = 362.34	Dx = 1.416 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2745 reflections
a = 13.6764 (6) Å	θ = 1.1–25.0°
b = 6.9852 (3) Å	µ = 0.10 mm^−1
c = 37.9306 (18) Å	T = 297 K
β = 110.253 (3)°	Plate, light_orange
V = 3399.6 (3) Å^3	0.36 × 0.29 × 0.12 mm
Z = 8

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	6003 independent reflections
Radiation source: fine-focus sealed tube	2866 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.1°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.964, Tmax = 0.988	l = −45→44
35803 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.250	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1037P)^2 + 1.1324P] where P = (Fo^2 + 2Fc^2)/3
6003 reflections	(Δ/σ)max < 0.001
495 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	−0.0077 (2)	−0.0655 (5)	0.59410 (9)	0.0608 (9)
O2A	−0.1209 (2)	−0.0375 (5)	0.62153 (9)	0.0671 (10)
O3A	−0.0309 (3)	0.1737 (6)	0.74766 (10)	0.0852 (13)
O4A	0.1296 (3)	0.2227 (6)	0.78133 (10)	0.0882 (13)
N1A	0.2973 (3)	−0.0472 (5)	0.63932 (10)	0.0457 (9)
N2A	0.1913 (3)	−0.0260 (5)	0.63201 (11)	0.0462 (10)
N3A	−0.0304 (3)	−0.0310 (5)	0.62228 (11)	0.0487 (10)
N4A	0.0623 (4)	0.1761 (6)	0.75165 (12)	0.0612 (11)
C1A	0.5021 (4)	−0.1676 (6)	0.65506 (13)	0.0515 (12)
H1A	0.4741	−0.1831	0.6740	0.062*
C2A	0.6080 (4)	−0.1940 (7)	0.66303 (16)	0.0627 (14)
H2A	0.6505	−0.2281	0.6872	0.075*
C3A	0.6504 (4)	−0.1699 (7)	0.63527 (19)	0.0714 (16)
H3A	0.7216	−0.1858	0.6406	0.086*
C4A	0.5871 (4)	−0.1228 (7)	0.59994 (18)	0.0662 (15)
H4A	0.6153	−0.1083	0.5810	0.079*
C5A	0.4809 (4)	−0.0960 (7)	0.59179 (14)	0.0577 (13)
H5A	0.4386	−0.0626	0.5676	0.069*
C6A	0.4380 (3)	−0.1186 (6)	0.61947 (13)	0.0445 (11)
C7A	0.3248 (3)	−0.0834 (6)	0.61092 (13)	0.0442 (11)
C8A	0.2525 (3)	−0.0875 (7)	0.57119 (12)	0.0452 (11)
C9A	0.2229 (4)	−0.2593 (8)	0.55305 (14)	0.0640 (14)
H9A	0.2489	−0.3732	0.5655	0.077*
C10A	0.1541 (4)	−0.2636 (10)	0.51616 (16)	0.0826 (17)
H10A	0.1321	−0.3804	0.5043	0.099*
C11A	0.1190 (4)	−0.0982 (10)	0.49741 (16)	0.0754 (16)
H11A	0.0743	−0.1019	0.4725	0.090*
C12A	0.1491 (4)	0.0736 (9)	0.51486 (16)	0.0732 (16)
H12A	0.1252	0.1872	0.5020	0.088*
C13A	0.2149 (4)	0.0776 (7)	0.55157 (15)	0.0655 (14)
H13A	0.2346	0.1951	0.5635	0.079*
C14A	0.1579 (3)	0.0209 (6)	0.66027 (12)	0.0409 (11)
C15A	0.0513 (3)	0.0220 (6)	0.65716 (12)	0.0425 (11)
C16A	0.0205 (3)	0.0719 (6)	0.68696 (13)	0.0476 (12)
H16A	−0.0497	0.0708	0.6842	0.057*
C17A	0.0936 (3)	0.1227 (6)	0.72036 (12)	0.0459 (11)
C18A	0.1995 (3)	0.1237 (7)	0.72493 (13)	0.0530 (12)
H18A	0.2490	0.1588	0.7478	0.064*
C19A	0.2298 (3)	0.0726 (6)	0.69541 (12)	0.0498 (12)
H19A	0.3004	0.0722	0.6988	0.060*
O2B	0.3749 (3)	0.3936 (5)	0.62378 (9)	0.0692 (10)
O3B	0.4694 (3)	0.1804 (6)	0.74998 (10)	0.0868 (13)
O4B	0.6300 (3)	0.1241 (6)	0.78269 (10)	0.0847 (12)
N1B	0.7906 (3)	0.3905 (5)	0.63908 (10)	0.0464 (9)
N2B	0.6860 (3)	0.3689 (6)	0.63202 (12)	0.0487 (10)
N3B	0.4642 (3)	0.3754 (5)	0.62334 (11)	0.0488 (10)
N4B	0.5618 (4)	0.1719 (6)	0.75331 (12)	0.0600 (11)
C1B	0.9944 (3)	0.5229 (6)	0.65585 (13)	0.0494 (12)
H1B	0.9643	0.5504	0.6738	0.059*
C2B	1.1009 (4)	0.5427 (7)	0.66461 (14)	0.0607 (14)
H2B	1.1422	0.5828	0.6885	0.073*
C3B	1.1461 (4)	0.5033 (7)	0.63820 (17)	0.0655 (15)
H3B	1.2179	0.5143	0.6445	0.079*
C4B	1.0865 (4)	0.4486 (8)	0.60304 (17)	0.0691 (15)
H4B	1.1173	0.4239	0.5852	0.083*
C5B	0.9791 (4)	0.4294 (7)	0.59365 (13)	0.0552 (13)
H5B	0.9382	0.3944	0.5694	0.066*
C6B	0.9328 (3)	0.4623 (6)	0.62039 (12)	0.0442 (11)
C7B	0.8198 (3)	0.4309 (6)	0.61091 (13)	0.0442 (11)
C8B	0.7485 (3)	0.4391 (7)	0.57110 (13)	0.0502 (12)
C13B	0.7375 (4)	0.6045 (8)	0.55033 (15)	0.0634 (14)
H13B	0.7745	0.7139	0.5612	0.076*
C12B	0.6710 (5)	0.6074 (10)	0.51316 (17)	0.0823 (18)
H12B	0.6632	0.7195	0.4992	0.099*
C11B	0.6169 (4)	0.4462 (12)	0.49681 (17)	0.087 (2)
H11B	0.5726	0.4492	0.4719	0.104*
C10B	0.6280 (4)	0.2828 (11)	0.51700 (16)	0.090 (2)
H10B	0.5915	0.1734	0.5059	0.108*
C9B	0.6938 (4)	0.2785 (8)	0.55419 (14)	0.0683 (15)
H9B	0.7012	0.1657	0.5679	0.082*
C14B	0.6536 (3)	0.3218 (6)	0.66095 (12)	0.0396 (11)
C15B	0.5462 (3)	0.3243 (6)	0.65786 (12)	0.0398 (11)
C16B	0.5180 (3)	0.2789 (6)	0.68813 (12)	0.0444 (11)
H16B	0.4482	0.2836	0.6860	0.053*
C17B	0.5916 (3)	0.2270 (6)	0.72137 (12)	0.0439 (11)
C18B	0.6970 (3)	0.2192 (6)	0.72522 (13)	0.0491 (12)
H18B	0.7467	0.1811	0.7478	0.059*
C19B	0.7261 (3)	0.2676 (6)	0.69568 (12)	0.0476 (12)
H19B	0.7965	0.2648	0.6986	0.057*
O1B	0.4854 (2)	0.3993 (5)	0.59473 (9)	0.0642 (10)
H2C	0.148 (4)	−0.067 (7)	0.6083 (13)	0.073 (16)*
H2D	0.640 (4)	0.386 (7)	0.6109 (13)	0.065 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.048 (2)	0.087 (3)	0.046 (2)	0.0039 (17)	0.0152 (17)	−0.0057 (18)
O2A	0.035 (2)	0.089 (3)	0.075 (2)	−0.0021 (17)	0.0177 (18)	−0.0147 (19)
O3A	0.051 (2)	0.143 (4)	0.071 (3)	0.014 (2)	0.033 (2)	−0.010 (2)
O4A	0.065 (3)	0.149 (4)	0.050 (2)	0.008 (2)	0.019 (2)	−0.019 (2)
N1A	0.036 (2)	0.055 (2)	0.051 (2)	−0.0035 (17)	0.0209 (19)	−0.0009 (19)
N2A	0.036 (2)	0.061 (3)	0.044 (3)	0.0005 (18)	0.017 (2)	−0.004 (2)
N3A	0.040 (3)	0.050 (2)	0.055 (3)	0.0066 (18)	0.016 (2)	0.002 (2)
N4A	0.055 (3)	0.086 (3)	0.048 (3)	0.014 (2)	0.026 (2)	0.002 (2)
C1A	0.050 (3)	0.055 (3)	0.051 (3)	−0.003 (2)	0.019 (3)	−0.007 (2)
C2A	0.040 (3)	0.058 (3)	0.080 (4)	0.008 (2)	0.007 (3)	−0.001 (3)
C3A	0.037 (3)	0.066 (4)	0.116 (5)	−0.001 (3)	0.034 (4)	−0.010 (3)
C4A	0.062 (4)	0.059 (3)	0.096 (5)	−0.003 (3)	0.051 (4)	−0.001 (3)
C5A	0.042 (3)	0.067 (3)	0.070 (4)	−0.006 (2)	0.028 (3)	−0.003 (3)
C6A	0.043 (3)	0.047 (3)	0.047 (3)	−0.005 (2)	0.019 (2)	−0.005 (2)
C7A	0.039 (3)	0.051 (3)	0.049 (3)	−0.003 (2)	0.024 (2)	−0.001 (2)
C8A	0.035 (3)	0.061 (3)	0.043 (3)	0.000 (2)	0.018 (2)	−0.005 (3)
C9A	0.062 (3)	0.068 (4)	0.059 (3)	0.004 (3)	0.017 (3)	−0.004 (3)
C10A	0.081 (4)	0.095 (5)	0.064 (4)	−0.005 (4)	0.015 (3)	−0.021 (4)
C11A	0.063 (4)	0.104 (5)	0.053 (3)	0.013 (4)	0.012 (3)	0.006 (4)
C12A	0.067 (4)	0.079 (4)	0.070 (4)	0.020 (3)	0.020 (3)	0.021 (3)
C13A	0.063 (3)	0.061 (4)	0.067 (4)	0.009 (3)	0.016 (3)	0.012 (3)
C14A	0.040 (3)	0.048 (3)	0.038 (3)	0.004 (2)	0.017 (2)	0.003 (2)
C15A	0.036 (3)	0.047 (3)	0.042 (3)	0.002 (2)	0.010 (2)	0.001 (2)
C16A	0.042 (3)	0.055 (3)	0.050 (3)	0.009 (2)	0.020 (2)	0.006 (2)
C17A	0.041 (3)	0.059 (3)	0.043 (3)	0.008 (2)	0.020 (2)	0.008 (2)
C18A	0.042 (3)	0.069 (3)	0.044 (3)	0.007 (2)	0.009 (2)	0.005 (2)
C19A	0.038 (3)	0.067 (3)	0.048 (3)	−0.002 (2)	0.020 (2)	−0.001 (2)
O2B	0.037 (2)	0.094 (3)	0.075 (2)	0.0068 (18)	0.0165 (18)	0.0112 (19)
O3B	0.054 (3)	0.144 (4)	0.073 (3)	−0.011 (2)	0.035 (2)	0.013 (2)
O4B	0.069 (3)	0.131 (3)	0.051 (2)	−0.013 (2)	0.016 (2)	0.019 (2)
N1B	0.031 (2)	0.055 (2)	0.053 (3)	−0.0040 (17)	0.0157 (18)	−0.0013 (19)
N2B	0.038 (3)	0.066 (3)	0.044 (3)	0.0016 (19)	0.016 (2)	0.003 (2)
N3B	0.044 (3)	0.048 (2)	0.049 (3)	0.0021 (18)	0.010 (2)	0.0048 (19)
N4B	0.055 (3)	0.079 (3)	0.051 (3)	−0.010 (2)	0.024 (2)	0.000 (2)
C1B	0.049 (3)	0.046 (3)	0.055 (3)	−0.005 (2)	0.020 (3)	0.001 (2)
C2B	0.044 (3)	0.063 (3)	0.063 (3)	−0.006 (2)	0.003 (3)	0.010 (3)
C3B	0.043 (3)	0.063 (4)	0.095 (5)	−0.003 (2)	0.029 (3)	0.007 (3)
C4B	0.057 (4)	0.078 (4)	0.087 (4)	0.010 (3)	0.042 (3)	0.003 (3)
C5B	0.046 (3)	0.071 (3)	0.052 (3)	−0.005 (2)	0.020 (2)	−0.004 (3)
C6B	0.039 (3)	0.050 (3)	0.050 (3)	−0.005 (2)	0.022 (2)	−0.001 (2)
C7B	0.041 (3)	0.046 (3)	0.049 (3)	0.002 (2)	0.021 (2)	0.002 (2)
C8B	0.039 (3)	0.069 (4)	0.046 (3)	0.003 (2)	0.019 (2)	−0.003 (3)
C13B	0.046 (3)	0.080 (4)	0.066 (4)	0.009 (3)	0.021 (3)	0.018 (3)
C12B	0.065 (4)	0.114 (5)	0.072 (4)	0.018 (4)	0.030 (4)	0.028 (4)
C11B	0.051 (4)	0.156 (7)	0.050 (4)	0.009 (4)	0.013 (3)	0.017 (4)
C10B	0.066 (4)	0.150 (6)	0.050 (4)	−0.023 (4)	0.016 (3)	−0.019 (4)
C9B	0.066 (4)	0.088 (4)	0.053 (3)	−0.009 (3)	0.025 (3)	−0.002 (3)
C14B	0.037 (3)	0.040 (3)	0.045 (3)	0.0011 (19)	0.018 (2)	−0.003 (2)
C15B	0.037 (3)	0.043 (3)	0.040 (3)	−0.0010 (19)	0.014 (2)	0.003 (2)
C16B	0.035 (3)	0.051 (3)	0.049 (3)	−0.001 (2)	0.017 (2)	−0.003 (2)
C17B	0.047 (3)	0.048 (3)	0.041 (3)	−0.007 (2)	0.022 (2)	−0.003 (2)
C18B	0.036 (3)	0.065 (3)	0.045 (3)	−0.002 (2)	0.013 (2)	0.000 (2)
C19B	0.032 (2)	0.067 (3)	0.044 (3)	−0.001 (2)	0.013 (2)	−0.001 (2)
O1B	0.053 (2)	0.093 (3)	0.047 (2)	0.0082 (18)	0.0166 (17)	0.0179 (19)

Geometric parameters (Å, º)

O1A—N3A	1.236 (4)	O2B—N3B	1.234 (4)
O2A—N3A	1.229 (4)	O3B—N4B	1.227 (5)
O3A—N4A	1.231 (5)	O4B—N4B	1.226 (5)
O4A—N4A	1.226 (5)	N1B—C7B	1.295 (5)
N1A—C7A	1.283 (5)	N1B—N2B	1.369 (5)
N1A—N2A	1.387 (5)	N2B—C14B	1.359 (5)
N2A—C14A	1.343 (5)	N2B—H2D	0.84 (5)
N2A—H2C	0.93 (5)	N3B—O1B	1.227 (4)
N3A—C15A	1.453 (5)	N3B—C15B	1.443 (5)
N4A—C17A	1.443 (5)	N4B—C17B	1.457 (5)
C1A—C6A	1.374 (6)	C1B—C6B	1.383 (6)
C1A—C2A	1.386 (6)	C1B—C2B	1.384 (6)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C3A	1.377 (7)	C2B—C3B	1.374 (6)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.360 (7)	C3B—C4B	1.355 (7)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.390 (6)	C4B—C5B	1.393 (6)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.378 (6)	C5B—C6B	1.388 (6)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.488 (6)	C6B—C7B	1.476 (6)
C7A—C8A	1.489 (6)	C7B—C8B	1.488 (6)
C8A—C13A	1.373 (6)	C8B—C13B	1.377 (6)
C8A—C9A	1.373 (6)	C8B—C9B	1.377 (7)
C9A—C10A	1.390 (7)	C13B—C12B	1.388 (7)
C9A—H9A	0.9300	C13B—H13B	0.9300
C10A—C11A	1.354 (8)	C12B—C11B	1.372 (8)
C10A—H10A	0.9300	C12B—H12B	0.9300
C11A—C12A	1.364 (7)	C11B—C10B	1.353 (8)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.372 (7)	C10B—C9B	1.386 (7)
C12A—H12A	0.9300	C10B—H10B	0.9300
C13A—H13A	0.9300	C9B—H9B	0.9300
C14A—C19A	1.402 (6)	C14B—C19B	1.400 (6)
C14A—C15A	1.421 (6)	C14B—C15B	1.433 (5)
C15A—C16A	1.381 (5)	C15B—C16B	1.368 (5)
C16A—C17A	1.361 (6)	C16B—C17B	1.362 (6)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.398 (6)	C17B—C18B	1.399 (5)
C18A—C19A	1.369 (6)	C18B—C19B	1.356 (5)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—H19A	0.9300	C19B—H19B	0.9300
C7A—N1A—N2A	116.3 (4)	C7B—N1B—N2B	117.5 (4)
C14A—N2A—N1A	119.2 (4)	C14B—N2B—N1B	118.7 (4)
C14A—N2A—H2C	125 (3)	C14B—N2B—H2D	118 (3)
N1A—N2A—H2C	115 (3)	N1B—N2B—H2D	124 (3)
O2A—N3A—O1A	121.7 (4)	O1B—N3B—O2B	122.4 (4)
O2A—N3A—C15A	118.8 (4)	O1B—N3B—C15B	119.3 (4)
O1A—N3A—C15A	119.5 (4)	O2B—N3B—C15B	118.3 (4)
O4A—N4A—O3A	122.2 (4)	O4B—N4B—O3B	122.6 (4)
O4A—N4A—C17A	118.8 (4)	O4B—N4B—C17B	119.0 (4)
O3A—N4A—C17A	119.0 (4)	O3B—N4B—C17B	118.4 (4)
C6A—C1A—C2A	120.7 (5)	C6B—C1B—C2B	120.1 (5)
C6A—C1A—H1A	119.6	C6B—C1B—H1B	120.0
C2A—C1A—H1A	119.6	C2B—C1B—H1B	120.0
C3A—C2A—C1A	120.1 (5)	C3B—C2B—C1B	120.4 (5)
C3A—C2A—H2A	119.9	C3B—C2B—H2B	119.8
C1A—C2A—H2A	119.9	C1B—C2B—H2B	119.8
C4A—C3A—C2A	119.4 (5)	C4B—C3B—C2B	120.3 (5)
C4A—C3A—H3A	120.3	C4B—C3B—H3B	119.8
C2A—C3A—H3A	120.3	C2B—C3B—H3B	119.8
C3A—C4A—C5A	120.7 (5)	C3B—C4B—C5B	120.0 (5)
C3A—C4A—H4A	119.6	C3B—C4B—H4B	120.0
C5A—C4A—H4A	119.6	C5B—C4B—H4B	120.0
C6A—C5A—C4A	120.3 (5)	C6B—C5B—C4B	120.3 (5)
C6A—C5A—H5A	119.9	C6B—C5B—H5B	119.8
C4A—C5A—H5A	119.9	C4B—C5B—H5B	119.8
C1A—C6A—C5A	118.8 (4)	C1B—C6B—C5B	118.8 (4)
C1A—C6A—C7A	121.1 (4)	C1B—C6B—C7B	121.1 (4)
C5A—C6A—C7A	120.0 (4)	C5B—C6B—C7B	120.1 (4)
N1A—C7A—C6A	115.8 (4)	N1B—C7B—C6B	115.3 (4)
N1A—C7A—C8A	124.7 (4)	N1B—C7B—C8B	124.3 (4)
C6A—C7A—C8A	119.6 (4)	C6B—C7B—C8B	120.3 (4)
C13A—C8A—C9A	118.2 (5)	C13B—C8B—C9B	118.9 (5)
C13A—C8A—C7A	121.7 (4)	C13B—C8B—C7B	121.1 (5)
C9A—C8A—C7A	120.1 (4)	C9B—C8B—C7B	120.1 (5)
C8A—C9A—C10A	120.2 (5)	C8B—C13B—C12B	119.8 (5)
C8A—C9A—H9A	119.9	C8B—C13B—H13B	120.1
C10A—C9A—H9A	119.9	C12B—C13B—H13B	120.1
C11A—C10A—C9A	120.3 (6)	C11B—C12B—C13B	120.6 (6)
C11A—C10A—H10A	119.9	C11B—C12B—H12B	119.7
C9A—C10A—H10A	119.9	C13B—C12B—H12B	119.7
C10A—C11A—C12A	120.2 (5)	C10B—C11B—C12B	119.9 (6)
C10A—C11A—H11A	119.9	C10B—C11B—H11B	120.0
C12A—C11A—H11A	119.9	C12B—C11B—H11B	120.0
C11A—C12A—C13A	119.5 (5)	C11B—C10B—C9B	120.0 (6)
C11A—C12A—H12A	120.3	C11B—C10B—H10B	120.0
C13A—C12A—H12A	120.3	C9B—C10B—H10B	120.0
C12A—C13A—C8A	121.6 (5)	C8B—C9B—C10B	120.8 (6)
C12A—C13A—H13A	119.2	C8B—C9B—H9B	119.6
C8A—C13A—H13A	119.2	C10B—C9B—H9B	119.6
N2A—C14A—C19A	120.1 (4)	N2B—C14B—C19B	120.1 (4)
N2A—C14A—C15A	123.9 (4)	N2B—C14B—C15B	122.9 (4)
C19A—C14A—C15A	116.0 (4)	C19B—C14B—C15B	117.0 (4)
C16A—C15A—C14A	121.9 (4)	C16B—C15B—C14B	120.4 (4)
C16A—C15A—N3A	116.9 (4)	C16B—C15B—N3B	117.6 (4)
C14A—C15A—N3A	121.2 (4)	C14B—C15B—N3B	122.0 (4)
C17A—C16A—C15A	119.6 (4)	C17B—C16B—C15B	120.4 (4)
C17A—C16A—H16A	120.2	C17B—C16B—H16B	119.8
C15A—C16A—H16A	120.2	C15B—C16B—H16B	119.8
C16A—C17A—C18A	120.8 (4)	C16B—C17B—C18B	120.7 (4)
C16A—C17A—N4A	120.2 (4)	C16B—C17B—N4B	120.7 (4)
C18A—C17A—N4A	119.1 (4)	C18B—C17B—N4B	118.5 (4)
C19A—C18A—C17A	119.4 (4)	C19B—C18B—C17B	119.4 (4)
C19A—C18A—H18A	120.3	C19B—C18B—H18B	120.3
C17A—C18A—H18A	120.3	C17B—C18B—H18B	120.3
C18A—C19A—C14A	122.3 (4)	C18B—C19B—C14B	122.0 (4)
C18A—C19A—H19A	118.9	C18B—C19B—H19B	119.0
C14A—C19A—H19A	118.9	C14B—C19B—H19B	119.0
C7A—N1A—N2A—C14A	−176.9 (4)	C7B—N1B—N2B—C14B	178.4 (4)
C6A—C1A—C2A—C3A	0.5 (7)	C6B—C1B—C2B—C3B	0.3 (7)
C1A—C2A—C3A—C4A	−0.9 (7)	C1B—C2B—C3B—C4B	1.4 (7)
C2A—C3A—C4A—C5A	1.0 (8)	C2B—C3B—C4B—C5B	−0.9 (8)
C3A—C4A—C5A—C6A	−0.6 (7)	C3B—C4B—C5B—C6B	−1.3 (7)
C2A—C1A—C6A—C5A	−0.1 (7)	C2B—C1B—C6B—C5B	−2.5 (6)
C2A—C1A—C6A—C7A	−177.9 (4)	C2B—C1B—C6B—C7B	177.0 (4)
C4A—C5A—C6A—C1A	0.1 (7)	C4B—C5B—C6B—C1B	3.0 (7)
C4A—C5A—C6A—C7A	178.0 (4)	C4B—C5B—C6B—C7B	−176.5 (4)
N2A—N1A—C7A—C6A	−176.1 (3)	N2B—N1B—C7B—C6B	177.0 (3)
N2A—N1A—C7A—C8A	5.3 (6)	N2B—N1B—C7B—C8B	−5.4 (6)
C1A—C6A—C7A—N1A	19.3 (6)	C1B—C6B—C7B—N1B	−25.7 (6)
C5A—C6A—C7A—N1A	−158.5 (4)	C5B—C6B—C7B—N1B	153.8 (4)
C1A—C6A—C7A—C8A	−162.1 (4)	C1B—C6B—C7B—C8B	156.7 (4)
C5A—C6A—C7A—C8A	20.1 (6)	C5B—C6B—C7B—C8B	−23.9 (6)
N1A—C7A—C8A—C13A	75.7 (6)	N1B—C7B—C8B—C13B	120.6 (5)
C6A—C7A—C8A—C13A	−102.8 (5)	C6B—C7B—C8B—C13B	−61.9 (6)
N1A—C7A—C8A—C9A	−105.2 (5)	N1B—C7B—C8B—C9B	−60.8 (6)
C6A—C7A—C8A—C9A	76.3 (5)	C6B—C7B—C8B—C9B	116.6 (5)
C13A—C8A—C9A—C10A	−1.9 (7)	C9B—C8B—C13B—C12B	0.9 (7)
C7A—C8A—C9A—C10A	179.0 (4)	C7B—C8B—C13B—C12B	179.4 (4)
C8A—C9A—C10A—C11A	2.5 (8)	C8B—C13B—C12B—C11B	−0.6 (8)
C9A—C10A—C11A—C12A	−1.5 (9)	C13B—C12B—C11B—C10B	0.1 (9)
C10A—C11A—C12A—C13A	−0.2 (8)	C12B—C11B—C10B—C9B	0.2 (9)
C11A—C12A—C13A—C8A	0.8 (8)	C13B—C8B—C9B—C10B	−0.6 (7)
C9A—C8A—C13A—C12A	0.3 (7)	C7B—C8B—C9B—C10B	−179.2 (5)
C7A—C8A—C13A—C12A	179.4 (4)	C11B—C10B—C9B—C8B	0.1 (8)
N1A—N2A—C14A—C19A	8.5 (6)	N1B—N2B—C14B—C19B	−9.8 (6)
N1A—N2A—C14A—C15A	−171.5 (4)	N1B—N2B—C14B—C15B	170.2 (4)
N2A—C14A—C15A—C16A	−179.7 (4)	N2B—C14B—C15B—C16B	−178.8 (4)
C19A—C14A—C15A—C16A	0.3 (6)	C19B—C14B—C15B—C16B	1.2 (6)
N2A—C14A—C15A—N3A	0.6 (6)	N2B—C14B—C15B—N3B	0.7 (6)
C19A—C14A—C15A—N3A	−179.3 (4)	C19B—C14B—C15B—N3B	−179.2 (4)
O2A—N3A—C15A—C16A	−3.4 (6)	O1B—N3B—C15B—C16B	−173.2 (4)
O1A—N3A—C15A—C16A	175.6 (4)	O2B—N3B—C15B—C16B	6.9 (6)
O2A—N3A—C15A—C14A	176.3 (4)	O1B—N3B—C15B—C14B	7.3 (6)
O1A—N3A—C15A—C14A	−4.8 (6)	O2B—N3B—C15B—C14B	−172.7 (4)
C14A—C15A—C16A—C17A	0.3 (6)	C14B—C15B—C16B—C17B	−1.3 (6)
N3A—C15A—C16A—C17A	180.0 (4)	N3B—C15B—C16B—C17B	179.1 (4)
C15A—C16A—C17A—C18A	−0.4 (7)	C15B—C16B—C17B—C18B	0.0 (6)
C15A—C16A—C17A—N4A	179.7 (4)	C15B—C16B—C17B—N4B	−177.8 (4)
O4A—N4A—C17A—C16A	−179.5 (4)	O4B—N4B—C17B—C16B	179.3 (4)
O3A—N4A—C17A—C16A	0.5 (6)	O3B—N4B—C17B—C16B	−2.7 (6)
O4A—N4A—C17A—C18A	0.7 (6)	O4B—N4B—C17B—C18B	1.4 (6)
O3A—N4A—C17A—C18A	−179.4 (4)	O3B—N4B—C17B—C18B	179.4 (4)
C16A—C17A—C18A—C19A	−0.1 (7)	C16B—C17B—C18B—C19B	1.3 (7)
N4A—C17A—C18A—C19A	179.8 (4)	N4B—C17B—C18B—C19B	179.2 (4)
C17A—C18A—C19A—C14A	0.7 (7)	C17B—C18B—C19B—C14B	−1.4 (7)
N2A—C14A—C19A—C18A	179.2 (4)	N2B—C14B—C19B—C18B	−179.8 (4)
C15A—C14A—C19A—C18A	−0.8 (6)	C15B—C14B—C19B—C18B	0.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2C···O1A	0.93 (5)	2.01 (6)	2.616 (5)	121 (4)
N2B—H2D···O1B	0.84 (5)	1.99 (6)	2.624 (5)	132 (5)
C19A—H19A···O3B	0.93	2.56	3.301 (6)	136
C19B—H19B···O3A^i	0.93	2.53	3.290 (6)	139
C11B—H11B···O1B^ii	0.93	2.60	3.437 (7)	150

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