Ethyl 4-(tert-butyl-amino)-3-nitro-benzoate.

In the title compound, C(13)H(18)N(2)O(4), intra-molecular N-H⋯O, N-H⋯N and C-H⋯O (× 3) hydrogen bonds generate S(6) and S(5) ring motifs. There are two crystallographically independent mol-ecules (A and B) in the asymmetric unit. The nitro group is coplanar with the benzene ring, with O-N-C-C torsion angles of -0.33 (13) and 0.93 (14)° in mol-ecules A and B, respectively. In the crystal structure, neighbouring mol-ecules are linked together by inter-molecular C-H⋯O hydrogen bonds. In addition, the crystal structure is stabilized by π-π inter-actions with centroid-centroid distances ranging from 3.7853 (6) to 3.8625 (6) Å.

Related literature

For literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For values of bond lengths, see: Allen et al. (1987 ▶). For related literature, see, for example: Göker et al. (1998 ▶); Anderson (2005 ▶); Kakei et al. (1993 ▶).

Experimental

Crystal data

C13H18N2O4

M = 266.29

Monoclinic,

a = 16.0471 (5) Å

b = 6.6417 (2) Å

c = 30.0180 (9) Å

β = 121.688 (2)°

V = 2722.37 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.51 × 0.43 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.879, T max = 0.984

63326 measured reflections

8141 independent reflections

6368 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.04

8141 reflections

351 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802206X/at2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802206X/at2594Isup2.hkl

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

C13H18N2O4	F000 = 1136
Mr = 266.29	Dx = 1.299 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9969 reflections
a = 16.0471 (5) Å	θ = 2.5–30.1º
b = 6.6417 (2) Å	µ = 0.10 mm−1
c = 30.0180 (9) Å	T = 100.0 (1) K
β = 121.688 (2)º	Plate, yellow
V = 2722.37 (14) Å3	0.51 × 0.43 × 0.17 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	8141 independent reflections
Radiation source: fine-focus sealed tube	6368 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 100.0(1) K	θmax = 30.3º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −21→22
Tmin = 0.879, Tmax = 0.984	k = −9→9
63326 measured reflections	l = −41→42

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.787P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
8141 reflections	Δρmax = 0.53 e Å−3
351 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	Uiso*/Ueq
O1A	1.01188 (6)	0.50707 (13)	0.90700 (3)	0.02027 (18)
O2A	0.87073 (6)	0.53054 (14)	0.90534 (3)	0.02371 (19)
O3A	0.57249 (6)	0.54152 (13)	0.73478 (3)	0.02243 (18)
O4A	0.56803 (6)	0.54680 (13)	0.66152 (3)	0.02250 (18)
N1A	0.61441 (6)	0.54228 (13)	0.71013 (4)	0.01589 (18)
N2A	0.73120 (6)	0.54415 (13)	0.66080 (3)	0.01583 (18)
H2NA	0.6682	0.5497	0.6444	0.019*
C1A	0.76647 (7)	0.53258 (15)	0.79329 (4)	0.0143 (2)
H1A	0.7281	0.5335	0.8089	0.017*
C2A	0.72036 (7)	0.53705 (15)	0.73898 (4)	0.01349 (19)
C3A	0.77441 (7)	0.53716 (14)	0.71324 (4)	0.01347 (19)
C4A	0.87825 (7)	0.52932 (15)	0.74731 (4)	0.0151 (2)
H4A	0.9180	0.5271	0.7325	0.018*
C5A	0.92253 (7)	0.52490 (15)	0.80055 (4)	0.0149 (2)
H5A	0.9920	0.5204	0.8217	0.018*
C6A	0.86747 (7)	0.52682 (15)	0.82473 (4)	0.0142 (2)
C7A	0.91408 (8)	0.52224 (16)	0.88226 (4)	0.0159 (2)
C8A	1.06291 (8)	0.5008 (2)	0.96363 (4)	0.0252 (3)
H8A	1.0412	0.3828	0.9751	0.030*
H8B	1.0489	0.6242	0.9771	0.030*
C9A	1.17025 (9)	0.4861 (2)	0.98412 (5)	0.0347 (3)
H9A	1.2069	0.4877	1.0225	0.052*
H9B	1.1904	0.6006	0.9713	0.052*
H9C	1.1837	0.3603	0.9720	0.052*
C10A	0.77667 (8)	0.54745 (16)	0.62878 (4)	0.0163 (2)
C11A	0.83246 (8)	0.35165 (17)	0.63510 (4)	0.0203 (2)
H11A	0.7877	0.2370	0.6254	0.030*
H11B	0.8861	0.3373	0.6716	0.030*
H11C	0.8593	0.3555	0.6124	0.030*
C12A	0.68959 (9)	0.56150 (19)	0.57218 (4)	0.0233 (2)
H12A	0.6458	0.4465	0.5647	0.035*
H12B	0.7136	0.5600	0.5481	0.035*
H12C	0.6537	0.6869	0.5676	0.035*
C13A	0.84047 (8)	0.73502 (17)	0.64034 (4)	0.0195 (2)
H13A	0.8927	0.7359	0.6774	0.029*
H13B	0.8000	0.8560	0.6324	0.029*
H13C	0.8695	0.7331	0.6186	0.029*
O1B	0.49200 (5)	0.43211 (13)	0.10402 (3)	0.02139 (18)
O2B	0.63293 (6)	0.45058 (13)	0.10484 (3)	0.02286 (18)
O3B	0.93204 (6)	0.47400 (13)	0.27341 (3)	0.02111 (18)
O4B	0.93898 (6)	0.47557 (13)	0.34743 (3)	0.02151 (18)
N1B	0.89147 (6)	0.47252 (13)	0.29872 (4)	0.01529 (18)
N2B	0.77682 (6)	0.47199 (14)	0.34950 (3)	0.01565 (18)
H2NB	0.8407	0.4767	0.3671	0.019*
C1B	0.73817 (7)	0.46115 (15)	0.21633 (4)	0.01401 (19)
H1B	0.7757	0.4608	0.2002	0.017*
C2B	0.78566 (7)	0.46722 (15)	0.27069 (4)	0.01293 (19)
C3B	0.73273 (7)	0.46737 (15)	0.29702 (4)	0.01340 (19)
C4B	0.62889 (8)	0.46322 (16)	0.26366 (4)	0.0157 (2)
H4B	0.5900	0.4645	0.2790	0.019*
C5B	0.58317 (7)	0.45740 (15)	0.21029 (4)	0.0154 (2)
H5B	0.5137	0.4545	0.1895	0.019*
C6B	0.63721 (7)	0.45564 (15)	0.18553 (4)	0.01401 (19)
C7B	0.58976 (8)	0.44669 (16)	0.12800 (4)	0.0168 (2)
C8B	0.43816 (8)	0.4179 (2)	0.04737 (4)	0.0260 (3)
H8C	0.3751	0.3484	0.0350	0.031*
H8D	0.4762	0.3370	0.0365	0.031*
C9B	0.41883 (9)	0.6226 (2)	0.02271 (5)	0.0302 (3)
H9D	0.3804	0.6089	−0.0155	0.045*
H9E	0.4812	0.6888	0.0335	0.045*
H9F	0.3822	0.7038	0.0340	0.045*
C10B	0.73206 (8)	0.46992 (16)	0.38189 (4)	0.0172 (2)
C11B	0.67381 (8)	0.27595 (17)	0.37340 (4)	0.0217 (2)
H11D	0.6189	0.2698	0.3370	0.032*
H11E	0.6487	0.2747	0.3969	0.032*
H11F	0.7166	0.1593	0.3809	0.032*
C12B	0.81999 (9)	0.47351 (19)	0.43837 (4)	0.0246 (2)
H12D	0.8582	0.5964	0.4441	0.037*
H12E	0.8613	0.3555	0.4445	0.037*
H12F	0.7966	0.4710	0.4627	0.037*
C13B	0.66997 (8)	0.65807 (18)	0.37269 (5)	0.0222 (2)
H13D	0.7108	0.7784	0.3806	0.033*
H13E	0.6433	0.6541	0.3955	0.033*
H13F	0.6160	0.6623	0.3360	0.033*

	U11	U22	U33	U12	U13	U23
O1A	0.0132 (3)	0.0327 (5)	0.0134 (4)	0.0004 (3)	0.0059 (3)	−0.0014 (3)
O2A	0.0181 (4)	0.0365 (5)	0.0190 (4)	0.0000 (3)	0.0114 (3)	−0.0013 (3)
O3A	0.0154 (4)	0.0298 (5)	0.0260 (4)	0.0006 (3)	0.0135 (3)	0.0003 (3)
O4A	0.0136 (4)	0.0309 (5)	0.0186 (4)	0.0002 (3)	0.0055 (3)	−0.0002 (3)
N1A	0.0126 (4)	0.0142 (4)	0.0205 (4)	−0.0004 (3)	0.0084 (3)	−0.0004 (3)
N2A	0.0120 (4)	0.0192 (4)	0.0151 (4)	0.0004 (3)	0.0062 (3)	0.0003 (3)
C1A	0.0149 (5)	0.0111 (4)	0.0189 (5)	−0.0006 (3)	0.0104 (4)	−0.0004 (4)
C2A	0.0102 (4)	0.0119 (5)	0.0175 (5)	0.0002 (3)	0.0068 (4)	0.0002 (4)
C3A	0.0135 (4)	0.0099 (4)	0.0168 (5)	−0.0006 (3)	0.0078 (4)	−0.0003 (3)
C4A	0.0127 (4)	0.0155 (5)	0.0182 (5)	0.0003 (4)	0.0088 (4)	0.0005 (4)
C5A	0.0124 (4)	0.0145 (5)	0.0175 (5)	0.0003 (4)	0.0076 (4)	0.0006 (4)
C6A	0.0147 (5)	0.0131 (5)	0.0148 (5)	−0.0004 (4)	0.0077 (4)	−0.0005 (4)
C7A	0.0140 (5)	0.0160 (5)	0.0170 (5)	−0.0009 (4)	0.0075 (4)	−0.0013 (4)
C8A	0.0188 (5)	0.0421 (7)	0.0122 (5)	0.0004 (5)	0.0065 (4)	−0.0021 (5)
C9A	0.0184 (6)	0.0630 (10)	0.0180 (6)	0.0030 (6)	0.0063 (5)	−0.0027 (6)
C10A	0.0161 (5)	0.0183 (5)	0.0154 (5)	−0.0005 (4)	0.0088 (4)	0.0001 (4)
C11A	0.0208 (5)	0.0181 (5)	0.0240 (5)	−0.0002 (4)	0.0131 (4)	−0.0028 (4)
C12A	0.0212 (5)	0.0303 (6)	0.0157 (5)	−0.0009 (5)	0.0078 (4)	−0.0005 (4)
C13A	0.0205 (5)	0.0190 (5)	0.0203 (5)	−0.0011 (4)	0.0116 (4)	0.0018 (4)
O1B	0.0133 (4)	0.0343 (5)	0.0138 (4)	−0.0022 (3)	0.0053 (3)	0.0013 (3)
O2B	0.0181 (4)	0.0339 (5)	0.0178 (4)	0.0012 (3)	0.0102 (3)	−0.0004 (3)
O3B	0.0150 (4)	0.0280 (4)	0.0238 (4)	0.0003 (3)	0.0127 (3)	0.0009 (3)
O4B	0.0136 (4)	0.0302 (5)	0.0164 (4)	0.0002 (3)	0.0049 (3)	0.0004 (3)
N1B	0.0135 (4)	0.0134 (4)	0.0186 (4)	0.0001 (3)	0.0081 (3)	0.0002 (3)
N2B	0.0129 (4)	0.0195 (4)	0.0143 (4)	0.0001 (3)	0.0070 (3)	0.0001 (3)
C1B	0.0144 (4)	0.0125 (5)	0.0168 (5)	0.0004 (3)	0.0093 (4)	0.0006 (4)
C2B	0.0108 (4)	0.0113 (4)	0.0166 (5)	0.0003 (3)	0.0072 (4)	0.0007 (3)
C3B	0.0147 (5)	0.0101 (4)	0.0151 (5)	0.0004 (3)	0.0077 (4)	0.0010 (3)
C4B	0.0137 (4)	0.0173 (5)	0.0185 (5)	0.0004 (4)	0.0100 (4)	0.0005 (4)
C5B	0.0121 (4)	0.0151 (5)	0.0185 (5)	0.0000 (4)	0.0076 (4)	0.0007 (4)
C6B	0.0135 (4)	0.0133 (5)	0.0148 (5)	0.0000 (3)	0.0071 (4)	0.0009 (3)
C7B	0.0152 (5)	0.0170 (5)	0.0163 (5)	0.0001 (4)	0.0070 (4)	0.0007 (4)
C8B	0.0176 (5)	0.0410 (7)	0.0148 (5)	−0.0037 (5)	0.0055 (4)	−0.0017 (5)
C9B	0.0236 (6)	0.0469 (8)	0.0197 (6)	0.0022 (5)	0.0111 (5)	0.0074 (5)
C10B	0.0194 (5)	0.0187 (5)	0.0158 (5)	0.0009 (4)	0.0107 (4)	0.0007 (4)
C11B	0.0255 (6)	0.0209 (5)	0.0226 (5)	−0.0013 (4)	0.0154 (5)	0.0024 (4)
C12B	0.0265 (6)	0.0306 (6)	0.0152 (5)	0.0009 (5)	0.0099 (5)	0.0008 (4)
C13B	0.0242 (5)	0.0205 (5)	0.0251 (6)	0.0019 (4)	0.0151 (5)	−0.0022 (4)

O1A—C7A	1.3418 (13)	O1B—C7B	1.3424 (13)
O1A—C8A	1.4489 (13)	O1B—C8B	1.4503 (13)
O2A—C7A	1.2136 (13)	O2B—C7B	1.2125 (13)
O3A—N1A	1.2340 (12)	O3B—N1B	1.2332 (12)
O4A—N1A	1.2424 (12)	O4B—N1B	1.2443 (12)
N1A—C2A	1.4474 (13)	N1B—C2B	1.4462 (13)
N2A—C3A	1.3470 (13)	N2B—C3B	1.3463 (13)
N2A—C10A	1.4810 (13)	N2B—C10B	1.4816 (13)
N2A—H2NA	0.8617	N2B—H2NB	0.8733
C1A—C6A	1.3827 (14)	C1B—C6B	1.3809 (14)
C1A—C2A	1.3925 (14)	C1B—C2B	1.3924 (14)
C1A—H1A	0.9500	C1B—H1B	0.9500
C2A—C3A	1.4328 (14)	C2B—C3B	1.4321 (14)
C3A—C4A	1.4265 (14)	C3B—C4B	1.4238 (14)
C4A—C5A	1.3663 (14)	C4B—C5B	1.3683 (14)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.4076 (14)	C5B—C6B	1.4076 (14)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.4784 (14)	C6B—C7B	1.4778 (14)
C8A—C9A	1.4973 (17)	C8B—C9B	1.5003 (19)
C8A—H8A	0.9900	C8B—H8C	0.9900
C8A—H8B	0.9900	C8B—H8D	0.9900
C9A—H9A	0.9800	C9B—H9D	0.9800
C9A—H9B	0.9800	C9B—H9E	0.9800
C9A—H9C	0.9800	C9B—H9F	0.9800
C10A—C13A	1.5320 (15)	C10B—C13B	1.5302 (15)
C10A—C11A	1.5331 (15)	C10B—C11B	1.5323 (15)
C10A—C12A	1.5343 (15)	C10B—C12B	1.5338 (15)
C11A—H11A	0.9800	C11B—H11D	0.9800
C11A—H11B	0.9800	C11B—H11E	0.9800
C11A—H11C	0.9800	C11B—H11F	0.9800
C12A—H12A	0.9800	C12B—H12D	0.9800
C12A—H12B	0.9800	C12B—H12E	0.9800
C12A—H12C	0.9800	C12B—H12F	0.9800
C13A—H13A	0.9800	C13B—H13D	0.9800
C13A—H13B	0.9800	C13B—H13E	0.9800
C13A—H13C	0.9800	C13B—H13F	0.9800
Cg1···Cg2i	3.7853 (6)	Cg1···Cg2ii	3.8625 (6)
C7A—O1A—C8A	115.30 (9)	C7B—O1B—C8B	116.24 (9)
O3A—N1A—O4A	121.71 (9)	O3B—N1B—O4B	121.87 (9)
O3A—N1A—C2A	118.70 (9)	O3B—N1B—C2B	118.70 (9)
O4A—N1A—C2A	119.59 (9)	O4B—N1B—C2B	119.43 (9)
C3A—N2A—C10A	129.22 (9)	C3B—N2B—C10B	129.04 (9)
C3A—N2A—H2NA	113.4	C3B—N2B—H2NB	115.9
C10A—N2A—H2NA	117.3	C10B—N2B—H2NB	115.0
C6A—C1A—C2A	120.74 (9)	C6B—C1B—C2B	120.85 (9)
C6A—C1A—H1A	119.6	C6B—C1B—H1B	119.6
C2A—C1A—H1A	119.6	C2B—C1B—H1B	119.6
C1A—C2A—C3A	122.10 (9)	C1B—C2B—C3B	121.91 (9)
C1A—C2A—N1A	115.83 (9)	C1B—C2B—N1B	115.79 (9)
C3A—C2A—N1A	122.07 (9)	C3B—C2B—N1B	122.30 (9)
N2A—C3A—C4A	121.97 (9)	N2B—C3B—C4B	121.65 (9)
N2A—C3A—C2A	122.98 (9)	N2B—C3B—C2B	123.11 (9)
C4A—C3A—C2A	115.05 (9)	C4B—C3B—C2B	115.23 (9)
C5A—C4A—C3A	122.23 (10)	C5B—C4B—C3B	122.25 (9)
C5A—C4A—H4A	118.9	C5B—C4B—H4B	118.9
C3A—C4A—H4A	118.9	C3B—C4B—H4B	118.9
C4A—C5A—C6A	121.42 (9)	C4B—C5B—C6B	121.22 (9)
C4A—C5A—H5A	119.3	C4B—C5B—H5B	119.4
C6A—C5A—H5A	119.3	C6B—C5B—H5B	119.4
C1A—C6A—C5A	118.45 (9)	C1B—C6B—C5B	118.54 (9)
C1A—C6A—C7A	119.36 (9)	C1B—C6B—C7B	119.12 (9)
C5A—C6A—C7A	122.19 (9)	C5B—C6B—C7B	122.34 (9)
O2A—C7A—O1A	122.82 (10)	O2B—C7B—O1B	123.56 (10)
O2A—C7A—C6A	125.16 (10)	O2B—C7B—C6B	124.77 (10)
O1A—C7A—C6A	112.03 (9)	O1B—C7B—C6B	111.67 (9)
O1A—C8A—C9A	107.65 (9)	O1B—C8B—C9B	111.18 (11)
O1A—C8A—H8A	110.2	O1B—C8B—H8C	109.4
C9A—C8A—H8A	110.2	C9B—C8B—H8C	109.4
O1A—C8A—H8B	110.2	O1B—C8B—H8D	109.4
C9A—C8A—H8B	110.2	C9B—C8B—H8D	109.4
H8A—C8A—H8B	108.5	H8C—C8B—H8D	108.0
C8A—C9A—H9A	109.5	C8B—C9B—H9D	109.5
C8A—C9A—H9B	109.5	C8B—C9B—H9E	109.5
H9A—C9A—H9B	109.5	H9D—C9B—H9E	109.5
C8A—C9A—H9C	109.5	C8B—C9B—H9F	109.5
H9A—C9A—H9C	109.5	H9D—C9B—H9F	109.5
H9B—C9A—H9C	109.5	H9E—C9B—H9F	109.5
N2A—C10A—C13A	111.31 (9)	N2B—C10B—C13B	111.59 (9)
N2A—C10A—C11A	111.21 (9)	N2B—C10B—C11B	111.24 (9)
C13A—C10A—C11A	112.61 (9)	C13B—C10B—C11B	111.97 (9)
N2A—C10A—C12A	104.30 (8)	N2B—C10B—C12B	104.10 (9)
C13A—C10A—C12A	108.24 (9)	C13B—C10B—C12B	108.70 (9)
C11A—C10A—C12A	108.76 (9)	C11B—C10B—C12B	108.88 (9)
C10A—C11A—H11A	109.5	C10B—C11B—H11D	109.5
C10A—C11A—H11B	109.5	C10B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C10A—C11A—H11C	109.5	C10B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C10A—C12A—H12A	109.5	C10B—C12B—H12D	109.5
C10A—C12A—H12B	109.5	C10B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C10A—C12A—H12C	109.5	C10B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C10A—C13A—H13A	109.5	C10B—C13B—H13D	109.5
C10A—C13A—H13B	109.5	C10B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C10A—C13A—H13C	109.5	C10B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O4A	0.86	1.93	2.6299 (15)	138
N2A—H2NA···N1A	0.86	2.54	2.9361 (15)	109
N2B—H2NB···O4B	0.87	1.95	2.6355 (15)	134
N2B—H2NB···N1B	0.87	2.58	2.9419 (15)	106
C1A—H1A···O3A	0.95	2.31	2.6522 (16)	100
C1B—H1B···O3B	0.95	2.31	2.6498 (16)	100
C4A—H4A···O3Biii	0.95	2.50	3.4124 (17)	160
C4B—H4B···O3Aiv	0.95	2.42	3.2566 (18)	147
C5A—H5A···O1A	0.95	2.41	2.7326 (13)	100
C11A—H11A···O2Bv	0.98	2.55	3.4714 (17)	157
C11B—H11F···O2Aii	0.98	2.52	3.4446 (17)	158
C13B—H13D···O2Avi	0.98	2.60	3.5071 (17)	154

Table 1

Selected centroid–centroid distances (Å)

Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

Cg1⋯Cg2i	3.7853 (6)
Cg1⋯Cg2ii	3.8625 (6)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2NA⋯O4A	0.86	1.93	2.6299 (15)	138
N2A—H2NA⋯N1A	0.86	2.54	2.9361 (15)	109
N2B—H2NB⋯O4B	0.87	1.95	2.6355 (15)	134
N2B—H2NB⋯N1B	0.87	2.58	2.9419 (15)	106
C1A—H1A⋯O3A	0.95	2.31	2.6522 (16)	100
C1B—H1B⋯O3B	0.95	2.31	2.6498 (16)	100
C4A—H4A⋯O3Biii	0.95	2.50	3.4124 (17)	160
C4B—H4B⋯O3Aiv	0.95	2.42	3.2566 (18)	147
C5A—H5A⋯O1A	0.95	2.41	2.7326 (13)	100
C11A—H11A⋯O2Bv	0.98	2.55	3.4714 (17)	157
C11B—H11F⋯O2Aii	0.98	2.52	3.4446 (17)	158
C13B—H13D⋯O2Avi	0.98	2.60	3.5071 (17)	154

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