3-Methyl-1-benzofuran-2-carbohydrazide.

In the asymmetric unit of the title benzofuran derivative, C(10)H(10)N(2)O(2), there are three crystallograpically independent mol-ecules, which are slightly twisted; the dihedral angle between the benzofuran ring system and the plane of the carbohydrazide unit is 8.64 (11)° in one mol-ecule, whereas the dihedral angles are 9.58 (11) and 6.89 (10)° in the other two mol-ecules. In the crystal, the three independent mol-ecules are linked to each other through N-H⋯N hydrogen bonds, forming a trimer. The trimers are further linked by weak N-H⋯O and C-H⋯O hydrogen bonds into a three-dimensional network. π-π inter-actions with centroid-centroid distances in the range 3.4928 (11)-3.8561 (10) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to and the bioactivity of benzofuran derivatives, see: Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz, Mekawey & Dawood (2009 ▶); Abdel-Wahab et al. (2009 ▶); Dawood et al. (2005 ▶); Hu et al. (2011 ▶); Ryu et al. (2010 ▶); Ungwitayatorn et al. (2001 ▶). For related structures, see: Ma et al. (2010 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C10H10N2O2

M = 190.20

Monoclinic,

a = 10.9391 (4) Å

b = 18.1257 (6) Å

c = 14.1818 (5) Å

β = 94.157 (2)°

V = 2804.55 (17) Å3

Z = 12

Cu Kα radiation

μ = 0.80 mm−1

T = 296 K

0.59 × 0.58 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.651, T max = 0.946

19906 measured reflections

5271 independent reflections

3618 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.133

S = 1.00

5271 reflections

419 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013190/is5101sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013190/is5101Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013190/is5101Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H10N2O2	F(000) = 1200
Mr = 190.20	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 5217 reflections
a = 10.9391 (4) Å	θ = 4.0–69.9°
b = 18.1257 (6) Å	µ = 0.80 mm−1
c = 14.1818 (5) Å	T = 296 K
β = 94.157 (2)°	Plate, colorless
V = 2804.55 (17) Å3	0.59 × 0.58 × 0.07 mm
Z = 12

Bruker SMART APEXII CCD area-detector diffractometer	5271 independent reflections
Radiation source: fine-focus sealed tube	3618 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 69.9°, θmin = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
Tmin = 0.651, Tmax = 0.946	k = −21→22
19906 measured reflections	l = −17→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0825P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.003
5271 reflections	Δρmax = 0.23 e Å−3
419 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00139 (18)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
N1A	0.66559 (14)	0.25954 (9)	0.45740 (10)	0.0571 (4)
N2A	0.73238 (19)	0.22213 (10)	0.53133 (12)	0.0631 (4)
O1A	0.63038 (14)	0.15700 (7)	0.36927 (10)	0.0709 (4)
O2A	0.56996 (11)	0.34643 (6)	0.31969 (8)	0.0561 (3)
C1A	0.56634 (15)	0.27126 (9)	0.30302 (11)	0.0524 (4)
C2A	0.51543 (15)	0.25509 (10)	0.21547 (12)	0.0562 (4)
C3A	0.48558 (15)	0.32498 (10)	0.17160 (12)	0.0556 (4)
C4A	0.43569 (18)	0.34786 (13)	0.08226 (14)	0.0717 (6)
H4AA	0.4123	0.3136	0.0356	0.086*
C5A	0.42246 (19)	0.42181 (14)	0.06571 (16)	0.0810 (6)
H5AA	0.3910	0.4377	0.0065	0.097*
C6A	0.4547 (2)	0.47400 (13)	0.13506 (18)	0.0801 (6)
H6AA	0.4419	0.5238	0.1218	0.096*
C7A	0.50514 (18)	0.45342 (12)	0.22282 (15)	0.0685 (5)
H7AA	0.5279	0.4879	0.2694	0.082*
C8A	0.51987 (15)	0.37872 (10)	0.23764 (12)	0.0550 (4)
C9A	0.62203 (16)	0.22390 (10)	0.37883 (12)	0.0534 (4)
C10A	0.4931 (2)	0.18129 (11)	0.17137 (16)	0.0808 (6)
H10D	0.4948	0.1443	0.2198	0.121*
H10E	0.5557	0.1710	0.1291	0.121*
H10F	0.4144	0.1810	0.1367	0.121*
N1B	0.83956 (14)	0.29089 (8)	0.71808 (11)	0.0569 (4)
N2B	0.82765 (19)	0.36857 (9)	0.71889 (12)	0.0633 (4)
O1B	0.92755 (12)	0.28638 (7)	0.86711 (9)	0.0695 (4)
O2B	0.83348 (11)	0.14361 (6)	0.70444 (8)	0.0566 (3)
C1B	0.87755 (15)	0.17365 (9)	0.79039 (11)	0.0507 (4)
C2B	0.90239 (15)	0.12155 (10)	0.85708 (13)	0.0560 (4)
C3B	0.87230 (16)	0.05251 (10)	0.81085 (14)	0.0609 (5)
C4B	0.8743 (2)	−0.02149 (13)	0.8389 (2)	0.0897 (7)
H4BA	0.8995	−0.0349	0.9005	0.108*
C5B	0.8378 (3)	−0.07389 (13)	0.7722 (3)	0.1080 (10)
H5BA	0.8385	−0.1234	0.7897	0.130*
C6B	0.8001 (3)	−0.05510 (13)	0.6802 (2)	0.0974 (8)
H6BA	0.7776	−0.0923	0.6371	0.117*
C7B	0.7950 (2)	0.01714 (11)	0.65068 (18)	0.0770 (6)
H7BA	0.7685	0.0302	0.5892	0.092*
C8B	0.83170 (16)	0.06907 (10)	0.71809 (14)	0.0587 (4)
C9B	0.88443 (15)	0.25460 (10)	0.79526 (12)	0.0527 (4)
C10B	0.94992 (19)	0.13066 (13)	0.95756 (14)	0.0740 (6)
H10A	0.9272	0.1784	0.9798	0.111*
H10B	1.0376	0.1263	0.9622	0.111*
H10C	0.9155	0.0932	0.9955	0.111*
N1C	0.69717 (14)	0.46541 (9)	0.57073 (10)	0.0594 (4)
N2C	0.64389 (18)	0.42386 (9)	0.49354 (12)	0.0623 (4)
O1C	0.64284 (13)	0.57510 (7)	0.50655 (9)	0.0699 (4)
O2C	0.79491 (11)	0.52731 (6)	0.72827 (8)	0.0567 (3)
C1C	0.75346 (15)	0.57452 (9)	0.65594 (11)	0.0506 (4)
C2C	0.77132 (16)	0.64592 (9)	0.67945 (13)	0.0531 (4)
C3C	0.82728 (16)	0.64574 (10)	0.77463 (13)	0.0554 (4)
C4C	0.86680 (19)	0.69945 (12)	0.84080 (16)	0.0729 (6)
H4CA	0.8602	0.7494	0.8261	0.088*
C5C	0.9156 (2)	0.67689 (15)	0.92799 (16)	0.0819 (7)
H5CA	0.9427	0.7122	0.9723	0.098*
C6C	0.92547 (19)	0.60330 (15)	0.95160 (15)	0.0834 (7)
H6CA	0.9585	0.5901	1.0115	0.100*
C7C	0.88740 (19)	0.54871 (13)	0.88830 (14)	0.0730 (5)
H7CA	0.8938	0.4989	0.9037	0.088*
C8C	0.83918 (15)	0.57222 (10)	0.80065 (12)	0.0562 (4)
C9C	0.69353 (15)	0.53881 (9)	0.57113 (11)	0.0512 (4)
C10C	0.7425 (2)	0.71305 (11)	0.62159 (15)	0.0730 (6)
H10G	0.7081	0.6987	0.5601	0.110*
H10H	0.8162	0.7408	0.6153	0.110*
H10I	0.6846	0.7429	0.6521	0.110*
H1N1	0.6655 (17)	0.3094 (11)	0.4641 (14)	0.063 (6)*
H2N1	0.8052 (18)	0.2666 (11)	0.6644 (15)	0.069 (6)*
H3N1	0.7349 (17)	0.4363 (12)	0.6145 (15)	0.069 (6)*
H1N2	0.687 (2)	0.1863 (14)	0.5467 (18)	0.085 (8)*
H2N2	0.792 (2)	0.2002 (13)	0.5072 (17)	0.080 (8)*
H3N2	0.901 (2)	0.3877 (13)	0.7343 (17)	0.086 (7)*
H4N2	0.777 (2)	0.3793 (12)	0.7671 (17)	0.078 (7)*
H5N2	0.667 (2)	0.4472 (13)	0.4439 (18)	0.084 (7)*
H6N2	0.560 (2)	0.4227 (12)	0.4966 (14)	0.074 (6)*

	U11	U22	U33	U12	U13	U23
N1A	0.0717 (9)	0.0530 (8)	0.0446 (7)	0.0021 (7)	−0.0089 (7)	−0.0002 (6)
N2A	0.0743 (11)	0.0612 (9)	0.0518 (8)	0.0026 (9)	−0.0096 (8)	0.0054 (7)
O1A	0.0983 (10)	0.0501 (7)	0.0630 (7)	−0.0067 (6)	−0.0030 (7)	−0.0019 (6)
O2A	0.0668 (7)	0.0534 (7)	0.0465 (6)	−0.0018 (5)	−0.0076 (5)	−0.0024 (5)
C1A	0.0559 (9)	0.0535 (9)	0.0471 (8)	−0.0030 (7)	−0.0009 (7)	−0.0047 (7)
C2A	0.0533 (9)	0.0648 (11)	0.0500 (9)	−0.0054 (8)	−0.0002 (7)	−0.0090 (8)
C3A	0.0489 (9)	0.0718 (11)	0.0456 (8)	0.0015 (8)	−0.0012 (7)	−0.0016 (8)
C4A	0.0622 (11)	0.1009 (16)	0.0505 (10)	0.0052 (10)	−0.0048 (8)	−0.0012 (10)
C5A	0.0694 (12)	0.1060 (18)	0.0668 (12)	0.0175 (12)	−0.0008 (10)	0.0258 (13)
C6A	0.0745 (13)	0.0802 (14)	0.0854 (15)	0.0155 (11)	0.0048 (11)	0.0208 (12)
C7A	0.0692 (12)	0.0644 (12)	0.0717 (12)	0.0061 (9)	0.0025 (9)	0.0068 (10)
C8A	0.0489 (9)	0.0647 (10)	0.0510 (9)	0.0025 (8)	0.0004 (7)	0.0040 (8)
C9A	0.0574 (10)	0.0529 (9)	0.0498 (9)	−0.0076 (7)	0.0026 (7)	−0.0030 (7)
C10A	0.0981 (16)	0.0753 (13)	0.0661 (12)	−0.0077 (12)	−0.0138 (11)	−0.0197 (10)
N1B	0.0728 (9)	0.0451 (8)	0.0501 (8)	0.0014 (6)	−0.0125 (7)	0.0022 (6)
N2B	0.0806 (12)	0.0473 (8)	0.0595 (9)	−0.0021 (8)	−0.0122 (9)	0.0034 (7)
O1B	0.0821 (9)	0.0679 (8)	0.0548 (7)	−0.0060 (6)	−0.0213 (6)	−0.0025 (6)
O2B	0.0682 (8)	0.0521 (7)	0.0482 (6)	0.0001 (5)	−0.0049 (5)	0.0029 (5)
C1B	0.0499 (8)	0.0546 (9)	0.0464 (8)	0.0024 (7)	−0.0041 (7)	0.0038 (7)
C2B	0.0494 (9)	0.0615 (10)	0.0564 (9)	0.0061 (8)	−0.0003 (7)	0.0130 (8)
C3B	0.0552 (10)	0.0550 (10)	0.0726 (11)	0.0080 (8)	0.0057 (8)	0.0115 (9)
C4B	0.0939 (17)	0.0652 (14)	0.1089 (19)	0.0150 (12)	−0.0006 (14)	0.0312 (13)
C5B	0.117 (2)	0.0477 (12)	0.159 (3)	0.0043 (13)	0.009 (2)	0.0132 (16)
C6B	0.1091 (19)	0.0569 (13)	0.126 (2)	−0.0038 (12)	0.0069 (17)	−0.0131 (14)
C7B	0.0823 (14)	0.0633 (12)	0.0856 (15)	−0.0028 (10)	0.0065 (12)	−0.0092 (11)
C8B	0.0580 (10)	0.0490 (9)	0.0695 (11)	0.0038 (7)	0.0071 (8)	0.0024 (8)
C9B	0.0515 (9)	0.0557 (9)	0.0496 (8)	0.0002 (7)	−0.0041 (7)	0.0034 (8)
C10B	0.0720 (12)	0.0882 (14)	0.0593 (11)	0.0057 (10)	−0.0118 (9)	0.0227 (10)
N1C	0.0726 (10)	0.0529 (8)	0.0498 (8)	0.0019 (7)	−0.0151 (7)	−0.0022 (7)
N2C	0.0713 (11)	0.0607 (9)	0.0524 (8)	−0.0012 (8)	−0.0128 (8)	−0.0061 (7)
O1C	0.0846 (9)	0.0649 (8)	0.0573 (7)	0.0083 (7)	−0.0151 (6)	0.0084 (6)
O2C	0.0694 (7)	0.0503 (6)	0.0485 (6)	0.0037 (5)	−0.0082 (5)	−0.0003 (5)
C1C	0.0515 (9)	0.0513 (9)	0.0483 (8)	0.0039 (7)	−0.0004 (7)	0.0017 (7)
C2C	0.0500 (9)	0.0505 (9)	0.0592 (9)	−0.0001 (7)	0.0074 (7)	−0.0004 (7)
C3C	0.0483 (9)	0.0595 (10)	0.0585 (9)	−0.0050 (7)	0.0045 (7)	−0.0090 (8)
C4C	0.0694 (12)	0.0664 (12)	0.0832 (14)	−0.0098 (10)	0.0067 (11)	−0.0193 (10)
C5C	0.0709 (13)	0.1076 (19)	0.0653 (12)	−0.0078 (12)	−0.0072 (10)	−0.0302 (12)
C6C	0.0697 (13)	0.121 (2)	0.0577 (11)	0.0053 (13)	−0.0098 (10)	−0.0120 (12)
C7C	0.0753 (12)	0.0858 (14)	0.0557 (10)	0.0078 (10)	−0.0100 (9)	−0.0016 (10)
C8C	0.0551 (9)	0.0620 (10)	0.0505 (9)	0.0020 (8)	−0.0031 (7)	−0.0083 (8)
C9C	0.0508 (9)	0.0542 (9)	0.0484 (9)	0.0046 (7)	0.0012 (7)	0.0029 (7)
C10C	0.0824 (14)	0.0541 (10)	0.0826 (14)	0.0009 (9)	0.0056 (11)	0.0101 (10)

N1A—C9A	1.345 (2)	C3B—C4B	1.399 (3)
N1A—N2A	1.408 (2)	C4B—C5B	1.378 (4)
N1A—H1N1	0.908 (19)	C4B—H4BA	0.9300
N2A—H1N2	0.86 (3)	C5B—C6B	1.383 (4)
N2A—H2N2	0.86 (2)	C5B—H5BA	0.9300
O1A—C9A	1.224 (2)	C6B—C7B	1.374 (3)
O2A—C8A	1.380 (2)	C6B—H6BA	0.9300
O2A—C1A	1.3829 (19)	C7B—C8B	1.380 (3)
C1A—C2A	1.355 (2)	C7B—H7BA	0.9300
C1A—C9A	1.473 (2)	C10B—H10A	0.9600
C2A—C3A	1.438 (3)	C10B—H10B	0.9600
C2A—C10A	1.489 (3)	C10B—H10C	0.9600
C3A—C8A	1.384 (2)	N1C—C9C	1.331 (2)
C3A—C4A	1.405 (2)	N1C—N2C	1.419 (2)
C4A—C5A	1.367 (3)	N1C—H3N1	0.89 (2)
C4A—H4AA	0.9300	N2C—H5N2	0.87 (2)
C5A—C6A	1.392 (3)	N2C—H6N2	0.92 (2)
C5A—H5AA	0.9300	O1C—C9C	1.227 (2)
C6A—C7A	1.376 (3)	O2C—C8C	1.371 (2)
C6A—H6AA	0.9300	O2C—C1C	1.3867 (19)
C7A—C8A	1.378 (3)	C1C—C2C	1.347 (2)
C7A—H7AA	0.9300	C1C—C9C	1.477 (2)
C10A—H10D	0.9600	C2C—C3C	1.441 (3)
C10A—H10E	0.9600	C2C—C10C	1.488 (2)
C10A—H10F	0.9600	C3C—C8C	1.386 (3)
N1B—C9B	1.339 (2)	C3C—C4C	1.399 (3)
N1B—N2B	1.414 (2)	C4C—C5C	1.373 (3)
N1B—H2N1	0.93 (2)	C4C—H4CA	0.9300
N2B—H3N2	0.88 (2)	C5C—C6C	1.378 (3)
N2B—H4N2	0.93 (2)	C5C—H5CA	0.9300
O1B—C9B	1.234 (2)	C6C—C7C	1.380 (3)
O2B—C8B	1.365 (2)	C6C—H6CA	0.9300
O2B—C1B	1.389 (2)	C7C—C8C	1.382 (2)
C1B—C2B	1.350 (2)	C7C—H7CA	0.9300
C1B—C9B	1.471 (2)	C10C—H10G	0.9600
C2B—C3B	1.440 (3)	C10C—H10H	0.9600
C2B—C10B	1.490 (3)	C10C—H10I	0.9600
C3B—C8B	1.391 (3)
C9A—N1A—N2A	121.28 (16)	C4B—C5B—H5BA	119.0
C9A—N1A—H1N1	124.1 (13)	C6B—C5B—H5BA	119.0
N2A—N1A—H1N1	113.9 (13)	C7B—C6B—C5B	121.6 (2)
N1A—N2A—H1N2	105.9 (16)	C7B—C6B—H6BA	119.2
N1A—N2A—H2N2	107.2 (16)	C5B—C6B—H6BA	119.2
H1N2—N2A—H2N2	103 (2)	C6B—C7B—C8B	115.8 (2)
C8A—O2A—C1A	105.61 (13)	C6B—C7B—H7BA	122.1
C2A—C1A—O2A	111.99 (15)	C8B—C7B—H7BA	122.1
C2A—C1A—C9A	131.56 (16)	O2B—C8B—C7B	125.68 (18)
O2A—C1A—C9A	116.38 (13)	O2B—C8B—C3B	109.94 (16)
C1A—C2A—C3A	105.73 (15)	C7B—C8B—C3B	124.39 (18)
C1A—C2A—C10A	128.52 (18)	O1B—C9B—N1B	122.75 (17)
C3A—C2A—C10A	125.75 (16)	O1B—C9B—C1B	121.31 (15)
C8A—C3A—C4A	118.09 (18)	N1B—C9B—C1B	115.92 (14)
C8A—C3A—C2A	106.57 (14)	C2B—C10B—H10A	109.5
C4A—C3A—C2A	135.32 (18)	C2B—C10B—H10B	109.5
C5A—C4A—C3A	118.3 (2)	H10A—C10B—H10B	109.5
C5A—C4A—H4AA	120.9	C2B—C10B—H10C	109.5
C3A—C4A—H4AA	120.9	H10A—C10B—H10C	109.5
C4A—C5A—C6A	121.81 (19)	H10B—C10B—H10C	109.5
C4A—C5A—H5AA	119.1	C9C—N1C—N2C	121.54 (14)
C6A—C5A—H5AA	119.1	C9C—N1C—H3N1	126.9 (13)
C7A—C6A—C5A	121.3 (2)	N2C—N1C—H3N1	111.5 (13)
C7A—C6A—H6AA	119.4	N1C—N2C—H5N2	103.8 (16)
C5A—C6A—H6AA	119.4	N1C—N2C—H6N2	109.3 (13)
C6A—C7A—C8A	116.1 (2)	H5N2—N2C—H6N2	113 (2)
C6A—C7A—H7AA	122.0	C8C—O2C—C1C	105.44 (13)
C8A—C7A—H7AA	122.0	C2C—C1C—O2C	112.09 (15)
C7A—C8A—O2A	125.48 (17)	C2C—C1C—C9C	132.11 (16)
C7A—C8A—C3A	124.43 (17)	O2C—C1C—C9C	115.72 (14)
O2A—C8A—C3A	110.09 (15)	C1C—C2C—C3C	105.88 (15)
O1A—C9A—N1A	122.86 (16)	C1C—C2C—C10C	128.88 (17)
O1A—C9A—C1A	121.78 (15)	C3C—C2C—C10C	125.23 (16)
N1A—C9A—C1A	115.33 (15)	C8C—C3C—C4C	118.17 (18)
C2A—C10A—H10D	109.5	C8C—C3C—C2C	106.07 (15)
C2A—C10A—H10E	109.5	C4C—C3C—C2C	135.75 (18)
H10D—C10A—H10E	109.5	C5C—C4C—C3C	118.6 (2)
C2A—C10A—H10F	109.5	C5C—C4C—H4CA	120.7
H10D—C10A—H10F	109.5	C3C—C4C—H4CA	120.7
H10E—C10A—H10F	109.5	C4C—C5C—C6C	121.7 (2)
C9B—N1B—N2B	120.72 (15)	C4C—C5C—H5CA	119.1
C9B—N1B—H2N1	122.5 (12)	C6C—C5C—H5CA	119.1
N2B—N1B—H2N1	116.3 (12)	C5C—C6C—C7C	121.4 (2)
N1B—N2B—H3N2	108.1 (15)	C5C—C6C—H6CA	119.3
N1B—N2B—H4N2	105.9 (14)	C7C—C6C—H6CA	119.3
H3N2—N2B—H4N2	108 (2)	C6C—C7C—C8C	116.2 (2)
C8B—O2B—C1B	105.74 (13)	C6C—C7C—H7CA	121.9
C2B—C1B—O2B	112.32 (16)	C8C—C7C—H7CA	121.9
C2B—C1B—C9B	131.15 (16)	O2C—C8C—C7C	125.56 (18)
O2B—C1B—C9B	116.47 (13)	O2C—C8C—C3C	110.51 (15)
C1B—C2B—C3B	105.15 (16)	C7C—C8C—C3C	123.92 (18)
C1B—C2B—C10B	129.11 (18)	O1C—C9C—N1C	123.01 (16)
C3B—C2B—C10B	125.75 (17)	O1C—C9C—C1C	121.52 (16)
C8B—C3B—C4B	118.2 (2)	N1C—C9C—C1C	115.47 (14)
C8B—C3B—C2B	106.85 (16)	C2C—C10C—H10G	109.5
C4B—C3B—C2B	134.9 (2)	C2C—C10C—H10H	109.5
C5B—C4B—C3B	117.9 (2)	H10G—C10C—H10H	109.5
C5B—C4B—H4BA	121.0	C2C—C10C—H10I	109.5
C3B—C4B—H4BA	121.0	H10G—C10C—H10I	109.5
C4B—C5B—C6B	122.0 (2)	H10H—C10C—H10I	109.5
C8A—O2A—C1A—C2A	−0.71 (19)	C1B—O2B—C8B—C7B	−179.46 (19)
C8A—O2A—C1A—C9A	176.44 (14)	C1B—O2B—C8B—C3B	0.71 (19)
O2A—C1A—C2A—C3A	0.9 (2)	C6B—C7B—C8B—O2B	−179.66 (19)
C9A—C1A—C2A—C3A	−175.65 (18)	C6B—C7B—C8B—C3B	0.2 (3)
O2A—C1A—C2A—C10A	−178.90 (18)	C4B—C3B—C8B—O2B	178.62 (17)
C9A—C1A—C2A—C10A	4.5 (3)	C2B—C3B—C8B—O2B	−0.7 (2)
C1A—C2A—C3A—C8A	−0.80 (19)	C4B—C3B—C8B—C7B	−1.2 (3)
C10A—C2A—C3A—C8A	179.05 (18)	C2B—C3B—C8B—C7B	179.49 (18)
C1A—C2A—C3A—C4A	177.5 (2)	N2B—N1B—C9B—O1B	−6.8 (3)
C10A—C2A—C3A—C4A	−2.7 (4)	N2B—N1B—C9B—C1B	172.22 (16)
C8A—C3A—C4A—C5A	−0.7 (3)	C2B—C1B—C9B—O1B	6.4 (3)
C2A—C3A—C4A—C5A	−178.8 (2)	O2B—C1B—C9B—O1B	−176.64 (16)
C3A—C4A—C5A—C6A	−1.2 (3)	C2B—C1B—C9B—N1B	−172.58 (18)
C4A—C5A—C6A—C7A	2.1 (3)	O2B—C1B—C9B—N1B	4.4 (2)
C5A—C6A—C7A—C8A	−0.8 (3)	C8C—O2C—C1C—C2C	0.82 (19)
C6A—C7A—C8A—O2A	179.05 (18)	C8C—O2C—C1C—C9C	−176.23 (15)
C6A—C7A—C8A—C3A	−1.2 (3)	O2C—C1C—C2C—C3C	−0.7 (2)
C1A—O2A—C8A—C7A	179.92 (17)	C9C—C1C—C2C—C3C	175.70 (18)
C1A—O2A—C8A—C3A	0.17 (18)	O2C—C1C—C2C—C10C	178.58 (17)
C4A—C3A—C8A—C7A	2.0 (3)	C9C—C1C—C2C—C10C	−5.0 (3)
C2A—C3A—C8A—C7A	−179.37 (17)	C1C—C2C—C3C—C8C	0.3 (2)
C4A—C3A—C8A—O2A	−178.24 (16)	C10C—C2C—C3C—C8C	−179.00 (17)
C2A—C3A—C8A—O2A	0.39 (19)	C1C—C2C—C3C—C4C	−178.5 (2)
N2A—N1A—C9A—O1A	4.9 (3)	C10C—C2C—C3C—C4C	2.1 (4)
N2A—N1A—C9A—C1A	−173.31 (17)	C8C—C3C—C4C—C5C	0.2 (3)
C2A—C1A—C9A—O1A	0.9 (3)	C2C—C3C—C4C—C5C	178.9 (2)
O2A—C1A—C9A—O1A	−175.59 (16)	C3C—C4C—C5C—C6C	−0.5 (3)
C2A—C1A—C9A—N1A	179.11 (18)	C4C—C5C—C6C—C7C	0.4 (3)
O2A—C1A—C9A—N1A	2.6 (2)	C5C—C6C—C7C—C8C	0.0 (3)
C8B—O2B—C1B—C2B	−0.49 (19)	C1C—O2C—C8C—C7C	178.43 (18)
C8B—O2B—C1B—C9B	−178.00 (14)	C1C—O2C—C8C—C3C	−0.59 (19)
O2B—C1B—C2B—C3B	0.1 (2)	C6C—C7C—C8C—O2C	−179.19 (18)
C9B—C1B—C2B—C3B	177.12 (17)	C6C—C7C—C8C—C3C	−0.3 (3)
O2B—C1B—C2B—C10B	−179.60 (18)	C4C—C3C—C8C—O2C	179.28 (16)
C9B—C1B—C2B—C10B	−2.6 (3)	C2C—C3C—C8C—O2C	0.2 (2)
C1B—C2B—C3B—C8B	0.4 (2)	C4C—C3C—C8C—C7C	0.2 (3)
C10B—C2B—C3B—C8B	−179.95 (18)	C2C—C3C—C8C—C7C	−178.86 (18)
C1B—C2B—C3B—C4B	−178.8 (2)	N2C—N1C—C9C—O1C	1.3 (3)
C10B—C2B—C3B—C4B	0.9 (3)	N2C—N1C—C9C—C1C	−179.64 (17)
C8B—C3B—C4B—C5B	1.1 (3)	C2C—C1C—C9C—O1C	−3.4 (3)
C2B—C3B—C4B—C5B	−179.9 (2)	O2C—C1C—C9C—O1C	172.87 (16)
C3B—C4B—C5B—C6B	0.1 (4)	C2C—C1C—C9C—N1C	177.44 (18)
C4B—C5B—C6B—C7B	−1.2 (4)	O2C—C1C—C9C—N1C	−6.2 (2)
C5B—C6B—C7B—C8B	1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1N1···N2C	0.91 (2)	2.13 (2)	3.034 (2)	171.4 (17)
N1B—H2N1···N2A	0.93 (2)	2.15 (2)	3.081 (2)	173.1 (17)
N1C—H3N1···N2B	0.89 (2)	2.12 (2)	3.016 (2)	179 (3)
N2A—H2N2···O1Bi	0.86 (2)	2.58 (2)	3.275 (2)	140 (2)
N2B—H4N2···O1Aii	0.93 (2)	2.33 (2)	3.176 (2)	150.4 (18)
N2C—H6N2···O1Ciii	0.92 (2)	2.22 (2)	3.137 (2)	175.5 (17)
C6A—H6AA···O1Aiv	0.93	2.55	3.444 (3)	162
C5C—H5CA···O1Bv	0.93	2.59	3.333 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1N1⋯N2C	0.91 (2)	2.13 (2)	3.034 (2)	171.4 (17)
N1B—H2N1⋯N2A	0.93 (2)	2.15 (2)	3.081 (2)	173.1 (17)
N1C—H3N1⋯N2B	0.89 (2)	2.12 (2)	3.016 (2)	179 (3)
N2A—H2N2⋯O1Bi	0.86 (2)	2.58 (2)	3.275 (2)	140 (2)
N2B—H4N2⋯O1Aii	0.93 (2)	2.33 (2)	3.176 (2)	150.4 (18)
N2C—H6N2⋯O1Ciii	0.92 (2)	2.22 (2)	3.137 (2)	175.5 (17)
C6A—H6AA⋯O1Aiv	0.93	2.55	3.444 (3)	162
C5C—H5CA⋯O1Bv	0.93	2.59	3.333 (3)	137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .