Hydrogen-bonding patterns in 2-amino-4,6-dimethyl­pyrimidine–cinnamic acid (1/2)

In the title compound, C₆H₉N₃·2C₉H₈O₂, an amino­pyrimidine–cinnamic acid 1:2 cocrystal, the 2-amino-4,6-dimethyl­pyrimidine mol­ecule forms two eight-membered hydrogen-bonded rings [R₂²(8) motif] with the carboxylic acid groups from two independent cinnamic acid mol­ecules via N—H...O and O—H...N hydrogen bonds. The cinnamic acid mol­ecules are linked by C—H...O hydrogen bonds to form chains along two axes.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.158
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.96 Deg.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2A    -   C9A     ..       5.13 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11A   -   C12A    ..       5.12 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C9A

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2-amino-4,6-dimethylpyrimidine–cinnamic acid (1/2)

Crystal data

C6H9N3·2C9H8O2	F(000) = 1776
Mr = 419.47	Dx = 1.241 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 25 reflections
a = 32.045 (2) Å	θ = 10.3–13.1°
b = 8.7676 (7) Å	µ = 0.09 mm^−1
c = 15.9796 (10) Å	T = 293 K
V = 4489.6 (5) Å^3	Plate-like, colourless
Z = 8	0.3 × 0.2 × 0.15 mm

Data collection

Enraf–Nonius MACH3 single-crystal diffractometer	2330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
w/–2q scans	h = −38→1
Absorption correction: ψ scan (North et al., 1968)	k = −1→10
Tmin = 0.970, Tmax = 0.982	l = −18→1
5035 measured reflections	1 standard reflections every 100 reflections
3956 independent reflections	intensity decay: none

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	Only H-atom displacement parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 1.8369P] where P = (Fo^2 + 2Fc^2)/3
3956 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.29314 (6)	−0.0599 (3)	0.91278 (14)	0.0854 (9)
O2A	0.26373 (6)	0.1248 (2)	0.98775 (14)	0.0826 (9)
C9A	0.26274 (9)	0.0114 (3)	0.93292 (18)	0.0632 (10)
C10A	0.22084 (9)	−0.0241 (4)	0.89966 (19)	0.0709 (11)
C11A	0.18873 (9)	0.0640 (4)	0.90727 (18)	0.0670 (11)
C12A	0.14599 (8)	0.0365 (3)	0.87587 (16)	0.0579 (9)
C13A	0.13321 (9)	−0.0987 (3)	0.83850 (17)	0.0612 (10)
C14A	0.09225 (10)	−0.1205 (3)	0.81564 (17)	0.0660 (10)
C15A	0.06323 (9)	−0.0080 (4)	0.82866 (18)	0.0715 (11)
C16A	0.07531 (10)	0.1282 (4)	0.8638 (2)	0.0780 (12)
C17A	0.11600 (10)	0.1487 (3)	0.88693 (19)	0.0721 (11)
O3B	0.48796 (6)	0.1782 (2)	0.95336 (13)	0.0743 (8)
O4B	0.45870 (6)	0.0107 (3)	0.86683 (13)	0.0765 (8)
C9B	0.48915 (9)	0.0774 (3)	0.89241 (17)	0.0592 (10)
C10B	0.53097 (8)	0.0539 (3)	0.85695 (17)	0.0620 (10)
C11B	0.56552 (8)	0.1167 (3)	0.88526 (16)	0.0567 (9)
C12B	0.60783 (8)	0.0963 (3)	0.85351 (16)	0.0562 (9)
C13B	0.64021 (9)	0.1824 (4)	0.88731 (19)	0.0699 (11)
C14B	0.68048 (9)	0.1663 (4)	0.8588 (2)	0.0803 (11)
C15B	0.68925 (9)	0.0644 (4)	0.7963 (2)	0.0784 (13)
C16B	0.65787 (9)	−0.0222 (4)	0.76268 (17)	0.0714 (11)
C17B	0.61764 (8)	−0.0077 (3)	0.79054 (16)	0.0623 (9)
N1	0.41366 (6)	0.2414 (2)	1.02048 (12)	0.0520 (7)
N2	0.37618 (7)	0.0663 (2)	0.94518 (13)	0.0585 (8)
N3	0.33999 (6)	0.2168 (2)	1.03765 (12)	0.0517 (7)
C2	0.37651 (7)	0.1771 (3)	1.00226 (14)	0.0478 (8)
C4	0.34103 (8)	0.3260 (3)	1.09614 (16)	0.0569 (9)
C5	0.37788 (8)	0.3948 (3)	1.11807 (18)	0.0641 (10)
C6	0.41415 (8)	0.3518 (3)	1.07830 (17)	0.0605 (9)
C7	0.30020 (9)	0.3665 (4)	1.1365 (2)	0.0768 (11)
C8	0.45543 (10)	0.4235 (5)	1.0967 (2)	0.0903 (16)
H2A	0.28800	0.14310	1.00050	0.108 (14)*
H10A	0.21740	−0.11600	0.87140	0.103 (12)*
H11A	0.19300	0.15530	0.93570	0.115 (13)*
H13A	0.15260	−0.17560	0.82890	0.084 (10)*
H14A	0.08420	−0.21220	0.79110	0.073 (8)*
H15A	0.03550	−0.02380	0.81380	0.086 (10)*
H16A	0.05590	0.20590	0.87170	0.087 (10)*
H17A	0.12380	0.24100	0.91100	0.082 (10)*
H3B	0.46380	0.18790	0.96970	0.094 (12)*
H10B	0.53320	−0.01030	0.81090	0.067 (8)*
H11B	0.56260	0.18160	0.93090	0.079 (9)*
H13B	0.63450	0.25190	0.92990	0.097 (11)*
H14B	0.70180	0.22480	0.88200	0.090 (11)*
H15B	0.71650	0.05400	0.77680	0.092 (10)*
H16B	0.66400	−0.09170	0.72040	0.083 (10)*
H17B	0.59670	−0.06770	0.76720	0.073 (9)*
H1	0.35310	0.02250	0.93200	0.078 (10)*
H2	0.39910	0.03860	0.92150	0.074 (9)*
H5	0.37840	0.46960	1.15930	0.088 (10)*
H7A	0.28280	0.41840	1.09670	0.128 (15)*
H7B	0.30520	0.43200	1.18360	0.130 (15)*
H7C	0.28640	0.27530	1.15510	0.160 (19)*
H8A	0.47490	0.34620	1.11360	0.16 (2)*
H8B	0.45230	0.49650	1.14110	0.122 (13)*
H8C	0.46570	0.47400	1.04750	0.17 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0612 (13)	0.0891 (16)	0.1058 (17)	−0.0091 (12)	0.0125 (12)	−0.0189 (13)
O2A	0.0547 (14)	0.0877 (16)	0.1054 (17)	0.0039 (11)	−0.0059 (11)	−0.0159 (14)
C9A	0.0615 (18)	0.0610 (17)	0.0671 (17)	−0.0074 (15)	0.0011 (14)	0.0044 (16)
C10A	0.0655 (18)	0.071 (2)	0.0763 (19)	−0.0096 (17)	0.0056 (14)	−0.0002 (17)
C11A	0.0674 (19)	0.0618 (18)	0.0717 (19)	−0.0009 (15)	0.0039 (14)	0.0054 (16)
C12A	0.0600 (16)	0.0565 (16)	0.0572 (16)	−0.0050 (13)	−0.0017 (12)	0.0065 (14)
C13A	0.0620 (18)	0.0590 (17)	0.0627 (17)	0.0019 (14)	0.0082 (13)	0.0052 (14)
C14A	0.076 (2)	0.0614 (17)	0.0606 (17)	−0.0125 (16)	0.0039 (14)	−0.0064 (14)
C15A	0.0613 (18)	0.085 (2)	0.0682 (18)	−0.0016 (18)	−0.0025 (14)	−0.0028 (17)
C16A	0.065 (2)	0.074 (2)	0.095 (2)	0.0157 (17)	−0.0057 (17)	−0.0092 (19)
C17A	0.075 (2)	0.0582 (18)	0.083 (2)	−0.0006 (15)	−0.0060 (16)	−0.0094 (16)
O3B	0.0534 (13)	0.0873 (14)	0.0823 (14)	0.0015 (10)	0.0051 (10)	−0.0251 (12)
O4B	0.0568 (12)	0.0919 (15)	0.0809 (13)	−0.0018 (12)	0.0001 (10)	−0.0221 (12)
C9B	0.0575 (18)	0.0628 (17)	0.0573 (16)	0.0062 (14)	−0.0023 (13)	−0.0002 (14)
C10B	0.0572 (17)	0.0710 (18)	0.0579 (16)	0.0049 (14)	0.0033 (12)	−0.0066 (15)
C11B	0.0536 (16)	0.0634 (16)	0.0532 (15)	0.0067 (13)	0.0007 (12)	0.0015 (14)
C12B	0.0549 (15)	0.0639 (16)	0.0498 (14)	0.0090 (13)	−0.0025 (12)	0.0099 (13)
C13B	0.0651 (19)	0.077 (2)	0.0676 (18)	0.0029 (16)	−0.0034 (14)	−0.0038 (17)
C14B	0.0530 (18)	0.095 (2)	0.093 (2)	−0.0063 (17)	−0.0009 (17)	0.001 (2)
C15B	0.0491 (17)	0.107 (3)	0.079 (2)	0.0078 (18)	0.0058 (15)	0.012 (2)
C16B	0.0674 (19)	0.091 (2)	0.0559 (17)	0.0161 (18)	0.0041 (14)	0.0034 (17)
C17B	0.0575 (16)	0.0754 (18)	0.0540 (15)	0.0070 (16)	−0.0041 (13)	0.0037 (15)
N1	0.0473 (12)	0.0567 (12)	0.0519 (12)	−0.0005 (10)	−0.0023 (9)	−0.0037 (11)
N2	0.0508 (13)	0.0620 (13)	0.0628 (13)	−0.0043 (11)	0.0052 (11)	−0.0104 (12)
N3	0.0460 (12)	0.0577 (12)	0.0514 (11)	0.0036 (10)	−0.0003 (9)	0.0016 (11)
C2	0.0501 (15)	0.0478 (13)	0.0456 (13)	0.0029 (12)	−0.0007 (11)	0.0042 (12)
C4	0.0526 (16)	0.0639 (16)	0.0541 (15)	0.0080 (13)	0.0019 (12)	−0.0001 (14)
C5	0.0599 (18)	0.0683 (18)	0.0641 (17)	0.0014 (15)	−0.0010 (13)	−0.0171 (15)
C6	0.0545 (16)	0.0681 (17)	0.0589 (16)	−0.0031 (14)	0.0000 (13)	−0.0073 (14)
C7	0.0584 (18)	0.095 (2)	0.077 (2)	0.0182 (18)	0.0076 (16)	−0.017 (2)
C8	0.063 (2)	0.108 (3)	0.100 (3)	−0.018 (2)	0.0004 (18)	−0.043 (2)

Geometric parameters (Å, º)

O1A—C9A	1.201 (4)	C17A—H17A	0.9302
O2A—C9A	1.326 (3)	C9B—C10B	1.470 (4)
O2A—H2A	0.8198	C10B—C11B	1.317 (4)
O3B—C9B	1.316 (3)	C11B—C12B	1.459 (4)
O4B—C9B	1.209 (4)	C12B—C17B	1.394 (4)
O3B—H3B	0.8215	C12B—C13B	1.392 (4)
N1—C6	1.338 (3)	C13B—C14B	1.376 (4)
N1—C2	1.349 (3)	C14B—C15B	1.369 (5)
N2—C2	1.333 (3)	C15B—C16B	1.370 (4)
N3—C2	1.346 (3)	C16B—C17B	1.370 (4)
N3—C4	1.338 (3)	C10B—H10B	0.9292
N2—H1	0.8596	C11B—H11B	0.9297
N2—H2	0.8612	C13B—H13B	0.9316
C9A—C10A	1.477 (4)	C14B—H14B	0.9313
C10A—C11A	1.292 (4)	C15B—H15B	0.9316
C11A—C12A	1.478 (4)	C16B—H16B	0.9308
C12A—C17A	1.387 (4)	C17B—H17B	0.9306
C12A—C13A	1.389 (4)	C4—C5	1.372 (4)
C13A—C14A	1.376 (4)	C4—C7	1.501 (4)
C14A—C15A	1.371 (4)	C5—C6	1.377 (4)
C15A—C16A	1.375 (5)	C6—C8	1.494 (4)
C16A—C17A	1.367 (5)	C5—H5	0.9298
C10A—H10A	0.9302	C7—H7A	0.9604
C11A—H11A	0.9305	C7—H7B	0.9602
C13A—H13A	0.9296	C7—H7C	0.9609
C14A—H14A	0.9310	C8—H8A	0.9600
C15A—H15A	0.9302	C8—H8B	0.9608
C16A—H16A	0.9311	C8—H8C	0.9604
O1A···N2	2.928 (3)	C14A···H5^viii	2.9793
O1A···C11A^i	3.349 (4)	C15A···H8B^viii	3.0398
O1A···C16B^ii	3.230 (4)	C17B···H10B	2.7255
O2A···N3	2.694 (3)	C17B···H14A^vii	3.0923
O2A···C7	3.392 (4)	H1···H17A^i	2.5985
O3B···N1	2.670 (3)	H1···C9A	2.8973
O3B···C9B^iii	3.411 (3)	H1···H2A	2.5823
O3B···C8	3.310 (4)	H1···O1A	2.0756
O4B···N2	2.966 (3)	H2···O4B	2.1144
O1A···H11A^i	2.5625	H2···H3B	2.5701
O1A···H16B^ii	2.5482	H2···C9B	2.9426
O1A···H1	2.0756	H2A···C4	2.7919
O2A···H11A	2.4291	H2A···N3	1.8830
O3B···H11B	2.4188	H2A···H1	2.5823
O4B···H2	2.1144	H2A···C7	2.9516
O4B···H10B^ii	2.8578	H2A···C2	2.8521
O4B···H17B^ii	2.8655	H3B···C2	2.8468
O4B···H16A^i	2.7141	H3B···C8	2.9081
N1···O3B	2.670 (3)	H3B···H2	2.5701
N2···O1A	2.928 (3)	H3B···C6	2.7583
N2···O4B	2.966 (3)	H3B···N1	1.8601
N2···C13A^iv	3.409 (3)	H5···H8B	2.3975
N3···O2A	2.694 (3)	H5···C14A^ix	2.9793
N1···H3B	1.8601	H5···H7B	2.4004
N2···H17A^i	2.9039	H7B···H5	2.4004
N3···H2A	1.8830	H8B···C15A^ix	3.0398
C2···C13A^iv	3.288 (4)	H8B···H5	2.3975
C2···C12B^iii	3.363 (4)	H10A···C13A	2.7528
C4···C16B^iii	3.491 (4)	H10A···H13A	2.2464
C4···C17B^iii	3.581 (4)	H10B···H17B	2.2094
C7···O2A	3.392 (4)	H10B···O4B^ii	2.8578
C8···O3B	3.310 (4)	H10B···C17B	2.7255
C9B···O3B^iii	3.411 (3)	H11A···H17A	2.3744
C11A···O1A^iv	3.349 (4)	H11A···O2A	2.4291
C12B···C2^iii	3.363 (4)	H11A···O1A^iv	2.5625
C13A···N2^i	3.409 (3)	H11B···O3B	2.4188
C13A···C2^i	3.288 (4)	H11B···H13B	2.3851
C16B···C4^iii	3.491 (4)	H13A···C10A	2.7973
C16B···O1A^ii	3.230 (4)	H13A···H10A	2.2464
C17B···C4^iii	3.581 (4)	H13B···H11B	2.3851
C2···H2A	2.8521	H13B···H17A^vi	2.5661
C2···H3B	2.8468	H14A···C12B^x	2.9550
C4···H2A	2.7919	H14A···C17B^x	3.0923
C6···H3B	2.7583	H15A···C8^v	3.0663
C7···H2A	2.9516	H15B···C7^vi	3.0983
C7···H15B^v	3.0983	H16A···O4B^iv	2.7141
C8···H3B	2.9081	H16B···O1A^ii	2.5482
C8···H15A^vi	3.0663	H17A···H11A	2.3744
C9A···H1	2.8973	H17A···N2^iv	2.9039
C9B···H2	2.9426	H17A···H1^iv	2.5985
C10A···H13A	2.7973	H17A···H13B^v	2.5661
C10B···H17B	2.7623	H17B···H10B	2.2094
C12B···H14A^vii	2.9550	H17B···O4B^ii	2.8655
C13A···H10A	2.7528	H17B···C10B	2.7623
C9A—O2A—H2A	109.50	C13B—C14B—C15B	120.1 (3)
C9B—O3B—H3B	109.40	C14B—C15B—C16B	119.8 (3)
C2—N1—C6	117.5 (2)	C15B—C16B—C17B	120.8 (3)
C2—N3—C4	117.2 (2)	C12B—C17B—C16B	120.5 (3)
C2—N2—H2	119.97	C9B—C10B—H10B	117.41
C2—N2—H1	120.02	C11B—C10B—H10B	117.43
H1—N2—H2	120.01	C12B—C11B—H11B	116.20
O1A—C9A—C10A	122.1 (3)	C10B—C11B—H11B	116.16
O2A—C9A—C10A	114.7 (2)	C14B—C13B—H13B	119.55
O1A—C9A—O2A	123.2 (3)	C12B—C13B—H13B	119.45
C9A—C10A—C11A	124.3 (3)	C13B—C14B—H14B	119.99
C10A—C11A—C12A	127.5 (3)	C15B—C14B—H14B	119.95
C13A—C12A—C17A	117.1 (2)	C16B—C15B—H15B	120.18
C11A—C12A—C17A	118.9 (3)	C14B—C15B—H15B	120.02
C11A—C12A—C13A	123.9 (3)	C15B—C16B—H16B	119.51
C12A—C13A—C14A	120.9 (3)	C17B—C16B—H16B	119.69
C13A—C14A—C15A	120.4 (3)	C12B—C17B—H17B	119.77
C14A—C15A—C16A	119.7 (3)	C16B—C17B—H17B	119.73
C15A—C16A—C17A	119.5 (3)	N1—C2—N2	117.3 (2)
C12A—C17A—C16A	122.2 (3)	N1—C2—N3	124.7 (2)
C9A—C10A—H10A	117.70	N2—C2—N3	118.0 (2)
C11A—C10A—H10A	117.97	C5—C4—C7	122.4 (2)
C12A—C11A—H11A	116.25	N3—C4—C5	121.0 (2)
C10A—C11A—H11A	116.30	N3—C4—C7	116.6 (2)
C12A—C13A—H13A	119.53	C4—C5—C6	119.2 (3)
C14A—C13A—H13A	119.54	N1—C6—C5	120.4 (2)
C15A—C14A—H14A	119.81	N1—C6—C8	116.8 (2)
C13A—C14A—H14A	119.75	C5—C6—C8	122.8 (3)
C16A—C15A—H15A	120.16	C4—C5—H5	120.45
C14A—C15A—H15A	120.13	C6—C5—H5	120.33
C15A—C16A—H16A	120.18	C4—C7—H7A	109.48
C17A—C16A—H16A	120.28	C4—C7—H7B	109.44
C12A—C17A—H17A	118.93	C4—C7—H7C	109.70
C16A—C17A—H17A	118.84	H7A—C7—H7B	109.42
O3B—C9B—O4B	123.5 (3)	H7A—C7—H7C	109.38
O3B—C9B—C10B	114.0 (2)	H7B—C7—H7C	109.39
O4B—C9B—C10B	122.5 (3)	C6—C8—H8A	109.50
C9B—C10B—C11B	125.2 (2)	C6—C8—H8B	109.47
C10B—C11B—C12B	127.6 (2)	C6—C8—H8C	109.65
C11B—C12B—C13B	119.4 (2)	H8A—C8—H8B	109.29
C13B—C12B—C17B	117.8 (2)	H8A—C8—H8C	109.45
C11B—C12B—C17B	122.7 (2)	H8B—C8—H8C	109.46
C12B—C13B—C14B	121.0 (3)
C2—N1—C6—C5	1.1 (4)	C14A—C15A—C16A—C17A	−1.3 (5)
C2—N1—C6—C8	−179.0 (2)	C15A—C16A—C17A—C12A	0.3 (5)
C6—N1—C2—N3	0.5 (4)	O3B—C9B—C10B—C11B	4.8 (4)
C6—N1—C2—N2	−179.4 (2)	O4B—C9B—C10B—C11B	−176.0 (3)
C2—N3—C4—C7	−178.6 (2)	C9B—C10B—C11B—C12B	179.1 (3)
C2—N3—C4—C5	0.6 (4)	C10B—C11B—C12B—C17B	−5.9 (4)
C4—N3—C2—N1	−1.3 (3)	C10B—C11B—C12B—C13B	174.7 (3)
C4—N3—C2—N2	178.6 (2)	C11B—C12B—C17B—C16B	179.8 (3)
O2A—C9A—C10A—C11A	14.4 (4)	C11B—C12B—C13B—C14B	−179.9 (3)
O1A—C9A—C10A—C11A	−167.2 (3)	C17B—C12B—C13B—C14B	0.7 (4)
C9A—C10A—C11A—C12A	−180.0 (3)	C13B—C12B—C17B—C16B	−0.8 (4)
C10A—C11A—C12A—C17A	−177.0 (3)	C12B—C13B—C14B—C15B	0.0 (5)
C10A—C11A—C12A—C13A	5.8 (5)	C13B—C14B—C15B—C16B	−0.5 (5)
C17A—C12A—C13A—C14A	−1.6 (4)	C14B—C15B—C16B—C17B	0.3 (5)
C11A—C12A—C13A—C14A	175.7 (3)	C15B—C16B—C17B—C12B	0.3 (4)
C11A—C12A—C17A—C16A	−176.3 (3)	N3—C4—C5—C6	0.9 (4)
C13A—C12A—C17A—C16A	1.1 (4)	C7—C4—C5—C6	−180.0 (3)
C12A—C13A—C14A—C15A	0.6 (4)	C4—C5—C6—C8	178.4 (3)
C13A—C14A—C15A—C16A	0.9 (4)	C4—C5—C6—N1	−1.7 (4)

Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x+1, y, −z+3/2; (iii) −x+1, −y, −z+2; (iv) −x+1/2, y+1/2, z; (v) x−1/2, −y+1/2, −z+2; (vi) x+1/2, −y+1/2, −z+2; (vii) x+1/2, y+1/2, −z+3/2; (viii) −x+1/2, −y+1/2, z−1/2; (ix) −x+1/2, −y+1/2, z+1/2; (x) x−1/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1A	0.86	2.08	2.928 (3)	171
N2—H2···O4B	0.86	2.11	2.966 (3)	170
O2A—H2A···N3	0.82	1.88	2.694 (3)	170
O3B—H3B···N1	0.82	1.86	2.670 (3)	168
C11A—H11A···O1A^iv	0.93	2.56	3.349 (4)	143
C16B—H16B···O1A^ii	0.93	2.55	3.230 (4)	130

Symmetry codes: (ii) −x+1, y, −z+3/2; (iv) −x+1/2, y+1/2, z.