Crystal structures of 4-phenyl­piperazin-1-ium 6-chloro-5-ethyl-2,4-dioxopyrimidin-1-ide and 4-phenyl­piperazin-1-ium 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide

In the crystals of the two novel piperazinium salts with a 6-chloro-5-ethyl-2,4-dioxopyrimidin-1-ide anion in (I) and a 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide anion in (II), the anions and cations are linked via N—H...O and N—H...N hydrogen bonds, forming sheets which are parallel to (100) in (I) and to (001) in (II). Salt (I) crystallizes with two independent 6-chloro-5-ethyl­uracil anions and two 1-phenyl­piperazine cations in the asymmetric unit.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.066
• wR factor = 0.185
• Data-to-parameter ratio = 15.6

Structure: II

• Single-crystal X-ray study
• T = 101 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.135
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0060 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A    ..  O1      ..       2.83 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.101 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          6 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C6 H6 Cl N2 O2
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         69 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   4 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
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT751_ALERT_4_C Bond    Calc     0.00000, Rep    0.000(5) ......  Senseless su
              N4   -N4      1.555   1.555 ............. Bond #          7 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #          4 Check
              N4   -N4   -C14     1.555   1.555   1.555              0.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #          5 Check
              N4   -N4   -C11     1.555   1.555   1.555              0.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         15 Check
              N4   -C11  -N4      1.555   1.555   1.555              0.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         34 Check
              N4   -C14  -N4      1.555   1.555   1.555              0.00 Deg.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C10 H15 N2
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         50 Note
PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by .          1 Units

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(I) 4-Phenylpiperazin-1-ium 6-chloro-5-ethyl-2,4-dioxopyrimidin-1-ide

Crystal data

C10H15N2^+·C6H6ClN2O2^−	F(000) = 1424
Mr = 336.82	Dx = 1.319 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 21.676 (1) Å	Cell parameters from 2418 reflections
b = 7.6446 (5) Å	θ = 4.1–70.3°
c = 20.5444 (8) Å	µ = 2.12 mm^−1
β = 95.065 (5)°	T = 293 K
V = 3391.0 (3) Å^3	Prism, colourless
Z = 8	0.17 × 0.08 × 0.06 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer	6532 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3596 reflections with I > 2σ(I)
Detector resolution: 10.2673 pixels mm^-1	Rint = 0.135
ω scans	θmax = 70.7°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −26→26
Tmin = 0.809, Tmax = 0.880	k = −9→9
32461 measured reflections	l = −21→25

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0563P)^2] where P = (Fo^2 + 2Fc^2)/3
6457 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.36 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.

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

	x	y	z	Uiso*/Ueq
Cl2	1.13235 (5)	0.04012 (14)	0.82294 (5)	0.0408 (3)
Cl1	0.65035 (5)	−0.09582 (15)	0.82219 (5)	0.0437 (3)
O1	0.51594 (14)	−0.6011 (4)	0.82514 (13)	0.0381 (7)
O2	0.55114 (13)	−0.3192 (4)	1.02030 (13)	0.0344 (7)
O3	1.04166 (14)	0.2995 (4)	1.02077 (13)	0.0378 (7)
N1	0.53525 (15)	−0.4583 (4)	0.92238 (15)	0.0288 (8)
H1	0.5119	−0.5322	0.9401	0.035*
O4	1.02351 (14)	0.5927 (4)	0.82725 (14)	0.0415 (8)
N7	1.03409 (15)	0.4421 (4)	0.92325 (15)	0.0306 (8)
H7	1.0140	0.5236	0.9410	0.037*
N2	0.57984 (15)	−0.3662 (4)	0.82841 (15)	0.0301 (8)
N8	1.07502 (16)	0.3338 (5)	0.82954 (16)	0.0330 (8)
N3	0.56236 (15)	0.6236 (4)	0.69138 (16)	0.0320 (8)
H3A	0.5695	0.6194	0.7347	0.038*
H3B	0.5338	0.7053	0.6817	0.038*
N4	0.64335 (15)	0.3661 (5)	0.64533 (16)	0.0330 (8)
N5	0.86014 (15)	0.0992 (4)	0.85634 (16)	0.0325 (8)
N6	0.93121 (15)	−0.1748 (4)	0.80703 (16)	0.0337 (8)
H6A	0.9565	−0.2655	0.8153	0.040*
H6B	0.9245	−0.1637	0.7639	0.040*
C1	0.54296 (19)	−0.4798 (5)	0.85679 (19)	0.0313 (9)
C18	1.05419 (19)	0.3021 (5)	0.9626 (2)	0.0328 (10)
C17	1.04364 (19)	0.4618 (6)	0.85811 (19)	0.0313 (9)
C4	0.60638 (18)	−0.2374 (5)	0.8663 (2)	0.0315 (9)
C2	0.56213 (18)	−0.3272 (5)	0.9617 (2)	0.0308 (9)
C20	1.09503 (18)	0.1988 (5)	0.8674 (2)	0.0309 (9)
C11	0.68606 (18)	0.2301 (5)	0.6354 (2)	0.0311 (9)
C9	0.6682 (2)	0.5311 (5)	0.6731 (2)	0.0345 (10)
H9A	0.7051	0.5634	0.6524	0.041*
H9B	0.6796	0.5166	0.7195	0.041*
C27	0.82314 (18)	0.2433 (5)	0.8709 (2)	0.0315 (9)
C3	0.60166 (18)	−0.2074 (5)	0.93082 (19)	0.0301 (9)
C25	0.82936 (19)	−0.0520 (5)	0.8253 (2)	0.0341 (10)
H25A	0.8201	−0.0296	0.7789	0.041*
H25B	0.7907	−0.0736	0.8443	0.041*
C19	1.08842 (19)	0.1695 (5)	0.93181 (19)	0.0316 (9)
C23	0.96153 (19)	−0.0141 (6)	0.8346 (2)	0.0357 (10)
H23A	0.9982	0.0104	0.8123	0.043*
H23B	0.9742	−0.0317	0.8806	0.043*
C21	1.1136 (2)	0.0116 (6)	0.9694 (2)	0.0377 (10)
H21A	1.1044	−0.0924	0.9433	0.045*
H21B	1.0928	0.0007	1.0091	0.045*
C28	0.7616 (2)	0.2637 (6)	0.8454 (2)	0.0397 (11)
H28	0.7448	0.1857	0.8139	0.048*
C10	0.62039 (19)	0.6734 (5)	0.6625 (2)	0.0336 (10)
H10A	0.6365	0.7809	0.6825	0.040*
H10B	0.6116	0.6941	0.6161	0.040*
C5	0.6318 (2)	−0.0569 (5)	0.9687 (2)	0.0359 (10)
H5A	0.6721	−0.0353	0.9533	0.043*
H5B	0.6381	−0.0893	1.0145	0.043*
C7	0.53832 (19)	0.4524 (6)	0.6672 (2)	0.0378 (10)
H7A	0.5248	0.4610	0.6211	0.045*
H7B	0.5029	0.4196	0.6903	0.045*
C16	0.74788 (19)	0.2396 (6)	0.6587 (2)	0.0357 (10)
H16	0.7618	0.3334	0.6849	0.043*
C15	0.7893 (2)	0.1105 (6)	0.6436 (2)	0.0412 (11)
H15	0.8308	0.1192	0.6592	0.049*
C26	0.87103 (19)	−0.2105 (6)	0.8348 (2)	0.0371 (10)
H26A	0.8784	−0.2368	0.8811	0.044*
H26B	0.8511	−0.3110	0.8132	0.044*
C12	0.6660 (2)	0.0859 (6)	0.5972 (2)	0.0369 (10)
H12	0.6246	0.0765	0.5812	0.044*
C8	0.58805 (18)	0.3138 (5)	0.6776 (2)	0.0344 (10)
H8A	0.5991	0.2979	0.7240	0.041*
H8B	0.5724	0.2033	0.6597	0.041*
C32	0.8473 (2)	0.3663 (5)	0.9167 (2)	0.0374 (10)
H32	0.8884	0.3573	0.9337	0.045*
C24	0.91766 (19)	0.1391 (6)	0.8266 (2)	0.0362 (10)
H24A	0.9370	0.2417	0.8473	0.043*
H24B	0.9083	0.1645	0.7805	0.043*
C29	0.7254 (2)	0.3984 (7)	0.8662 (2)	0.0480 (12)
H29	0.6843	0.4089	0.8493	0.058*
C31	0.8113 (2)	0.4999 (6)	0.9369 (2)	0.0442 (12)
H31	0.8282	0.5796	0.9677	0.053*
C13	0.7077 (2)	−0.0424 (6)	0.5832 (2)	0.0423 (11)
H13	0.6938	−0.1384	0.5582	0.051*
C22	1.1830 (2)	0.0208 (6)	0.9874 (2)	0.0433 (11)
H22A	1.1963	−0.0826	1.0111	0.065*
H22B	1.2040	0.0288	0.9483	0.065*
H22C	1.1924	0.1219	1.0141	0.065*
C14	0.7692 (2)	−0.0311 (6)	0.6054 (2)	0.0450 (12)
H14	0.7970	−0.1173	0.5948	0.054*
C30	0.7503 (2)	0.5173 (6)	0.9120 (2)	0.0487 (13)
H30	0.7261	0.6082	0.9259	0.058*
C6	0.5943 (2)	0.1094 (6)	0.9627 (2)	0.0529 (13)
H6C	0.6158	0.2002	0.9878	0.079*
H6D	0.5887	0.1440	0.9177	0.079*
H6E	0.5546	0.0899	0.9788	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl2	0.0470 (6)	0.0405 (6)	0.0359 (6)	0.0097 (5)	0.0099 (5)	−0.0029 (5)
Cl1	0.0503 (7)	0.0474 (7)	0.0347 (6)	−0.0174 (5)	0.0101 (5)	0.0010 (5)
O1	0.0488 (18)	0.0360 (17)	0.0301 (16)	−0.0110 (14)	0.0063 (14)	−0.0051 (13)
O2	0.0396 (17)	0.0410 (17)	0.0226 (15)	−0.0075 (13)	0.0030 (13)	0.0008 (12)
O3	0.0446 (18)	0.0400 (18)	0.0299 (16)	0.0085 (14)	0.0087 (14)	0.0022 (13)
N1	0.0337 (18)	0.0299 (18)	0.0231 (17)	−0.0075 (15)	0.0036 (14)	0.0018 (14)
O4	0.0462 (19)	0.0444 (19)	0.0349 (17)	0.0130 (15)	0.0087 (14)	0.0079 (14)
N7	0.0323 (18)	0.033 (2)	0.0266 (18)	0.0058 (15)	0.0057 (15)	−0.0034 (15)
N2	0.0301 (18)	0.036 (2)	0.0244 (17)	−0.0008 (15)	0.0033 (14)	0.0004 (15)
N8	0.0331 (19)	0.036 (2)	0.0305 (19)	0.0011 (16)	0.0053 (15)	−0.0007 (16)
N3	0.0349 (19)	0.0336 (19)	0.0280 (18)	0.0064 (15)	0.0052 (15)	−0.0001 (15)
N4	0.0304 (19)	0.033 (2)	0.0355 (19)	−0.0054 (15)	0.0046 (15)	−0.0023 (16)
N5	0.0297 (18)	0.0307 (19)	0.038 (2)	0.0003 (15)	0.0089 (16)	−0.0023 (16)
N6	0.038 (2)	0.035 (2)	0.0287 (19)	0.0004 (16)	0.0042 (16)	−0.0002 (15)
C1	0.032 (2)	0.033 (2)	0.028 (2)	−0.0028 (18)	0.0043 (18)	0.0009 (18)
C18	0.035 (2)	0.032 (2)	0.032 (2)	−0.0007 (18)	0.0079 (19)	0.0012 (18)
C17	0.032 (2)	0.035 (2)	0.028 (2)	0.0040 (18)	0.0048 (18)	0.0007 (18)
C4	0.027 (2)	0.035 (2)	0.033 (2)	−0.0055 (17)	0.0018 (18)	0.0043 (18)
C2	0.029 (2)	0.031 (2)	0.032 (2)	0.0002 (17)	0.0011 (18)	0.0027 (18)
C20	0.028 (2)	0.033 (2)	0.032 (2)	0.0001 (18)	0.0054 (18)	−0.0055 (18)
C11	0.029 (2)	0.033 (2)	0.032 (2)	0.0018 (18)	0.0075 (18)	0.0018 (18)
C9	0.039 (2)	0.029 (2)	0.036 (2)	−0.0052 (19)	0.009 (2)	−0.0006 (19)
C27	0.031 (2)	0.033 (2)	0.031 (2)	−0.0006 (18)	0.0070 (18)	0.0058 (18)
C3	0.031 (2)	0.033 (2)	0.026 (2)	−0.0006 (17)	−0.0008 (17)	0.0012 (17)
C25	0.032 (2)	0.038 (2)	0.032 (2)	−0.0057 (19)	0.0044 (18)	0.0012 (19)
C19	0.034 (2)	0.032 (2)	0.029 (2)	0.0009 (18)	0.0051 (18)	0.0000 (18)
C23	0.031 (2)	0.039 (3)	0.038 (2)	−0.0023 (19)	0.0063 (19)	−0.006 (2)
C21	0.042 (3)	0.038 (2)	0.035 (2)	0.006 (2)	0.010 (2)	0.004 (2)
C28	0.039 (2)	0.044 (3)	0.037 (3)	0.004 (2)	0.006 (2)	−0.001 (2)
C10	0.041 (2)	0.033 (2)	0.027 (2)	0.0013 (19)	0.0050 (19)	0.0011 (18)
C5	0.041 (2)	0.039 (3)	0.028 (2)	−0.009 (2)	0.0027 (19)	0.0014 (19)
C7	0.031 (2)	0.044 (3)	0.038 (2)	0.004 (2)	0.0009 (19)	−0.003 (2)
C16	0.034 (2)	0.038 (2)	0.036 (2)	0.0002 (19)	0.0054 (19)	−0.0014 (19)
C15	0.036 (2)	0.045 (3)	0.043 (3)	0.006 (2)	0.008 (2)	0.004 (2)
C26	0.038 (2)	0.039 (3)	0.034 (2)	−0.006 (2)	0.007 (2)	−0.0022 (19)
C12	0.040 (2)	0.037 (2)	0.034 (2)	0.000 (2)	0.0024 (19)	0.0026 (19)
C8	0.035 (2)	0.031 (2)	0.038 (2)	−0.0043 (19)	0.0045 (19)	−0.0033 (19)
C32	0.039 (2)	0.033 (2)	0.041 (3)	−0.0047 (19)	0.011 (2)	−0.002 (2)
C24	0.032 (2)	0.041 (3)	0.037 (2)	−0.0063 (19)	0.0111 (19)	−0.002 (2)
C29	0.044 (3)	0.055 (3)	0.045 (3)	0.015 (2)	0.006 (2)	0.005 (2)
C31	0.055 (3)	0.037 (3)	0.043 (3)	−0.001 (2)	0.017 (2)	−0.003 (2)
C13	0.058 (3)	0.034 (2)	0.037 (3)	−0.004 (2)	0.014 (2)	−0.006 (2)
C22	0.042 (3)	0.046 (3)	0.043 (3)	0.005 (2)	0.007 (2)	0.009 (2)
C14	0.053 (3)	0.037 (3)	0.047 (3)	0.010 (2)	0.017 (2)	0.002 (2)
C30	0.056 (3)	0.045 (3)	0.047 (3)	0.017 (2)	0.019 (3)	0.005 (2)
C6	0.065 (3)	0.040 (3)	0.051 (3)	0.002 (2)	−0.008 (3)	−0.010 (2)

Geometric parameters (Å, º)

Cl2—C20	1.758 (4)	C19—C21	1.509 (6)
Cl1—C4	1.747 (4)	C23—C24	1.508 (6)
O1—C1	1.249 (5)	C23—H23A	0.9700
O2—C2	1.248 (5)	C23—H23B	0.9700
O3—C18	1.249 (5)	C21—C22	1.517 (6)
N1—C1	1.382 (5)	C21—H21A	0.9700
N1—C2	1.384 (5)	C21—H21B	0.9700
N1—H1	0.8600	C28—C29	1.386 (6)
O4—C17	1.243 (5)	C28—H28	0.9300
N7—C17	1.380 (5)	C10—H10A	0.9700
N7—C18	1.388 (5)	C10—H10B	0.9700
N7—H7	0.8600	C5—C6	1.508 (6)
N2—C1	1.347 (5)	C5—H5A	0.9700
N2—C4	1.351 (5)	C5—H5B	0.9700
N8—C20	1.342 (5)	C7—C8	1.513 (6)
N8—C17	1.354 (5)	C7—H7A	0.9700
N3—C7	1.478 (5)	C7—H7B	0.9700
N3—C10	1.487 (5)	C16—C15	1.388 (6)
N3—H3A	0.8900	C16—H16	0.9300
N3—H3B	0.8900	C15—C14	1.385 (7)
N4—C11	1.419 (5)	C15—H15	0.9300
N4—C9	1.467 (5)	C26—H26A	0.9700
N4—C8	1.475 (5)	C26—H26B	0.9700
N5—C27	1.410 (5)	C12—C13	1.380 (6)
N5—C25	1.454 (5)	C12—H12	0.9300
N5—C24	1.468 (5)	C8—H8A	0.9700
N6—C23	1.482 (5)	C8—H8B	0.9700
N6—C26	1.495 (5)	C32—C31	1.371 (6)
N6—H6A	0.8900	C32—H32	0.9300
N6—H6B	0.8900	C24—H24A	0.9700
C18—C19	1.436 (6)	C24—H24B	0.9700
C4—C3	1.359 (6)	C29—C30	1.383 (7)
C2—C3	1.440 (6)	C29—H29	0.9300
C20—C19	1.362 (6)	C31—C30	1.383 (7)
C11—C16	1.385 (6)	C31—H31	0.9300
C11—C12	1.400 (6)	C13—C14	1.374 (7)
C9—C10	1.505 (6)	C13—H13	0.9300
C9—H9A	0.9700	C22—H22A	0.9600
C9—H9B	0.9700	C22—H22B	0.9600
C27—C28	1.398 (6)	C22—H22C	0.9600
C27—C32	1.399 (6)	C14—H14	0.9300
C3—C5	1.505 (6)	C30—H30	0.9300
C25—C26	1.514 (6)	C6—H6C	0.9600
C25—H25A	0.9700	C6—H6D	0.9600
C25—H25B	0.9700	C6—H6E	0.9600
C1—N1—C2	125.1 (3)	H21A—C21—H21B	107.8
C1—N1—H1	117.5	C29—C28—C27	121.0 (5)
C2—N1—H1	117.5	C29—C28—H28	119.5
C17—N7—C18	125.6 (3)	C27—C28—H28	119.5
C17—N7—H7	117.2	N3—C10—C9	110.7 (3)
C18—N7—H7	117.2	N3—C10—H10A	109.5
C1—N2—C4	117.3 (3)	C9—C10—H10A	109.5
C20—N8—C17	117.0 (3)	N3—C10—H10B	109.5
C7—N3—C10	112.2 (3)	C9—C10—H10B	109.5
C7—N3—H3A	109.2	H10A—C10—H10B	108.1
C10—N3—H3A	109.2	C3—C5—C6	113.3 (4)
C7—N3—H3B	109.2	C3—C5—H5A	108.9
C10—N3—H3B	109.2	C6—C5—H5A	108.9
H3A—N3—H3B	107.9	C3—C5—H5B	108.9
C11—N4—C9	117.6 (3)	C6—C5—H5B	108.9
C11—N4—C8	115.6 (3)	H5A—C5—H5B	107.7
C9—N4—C8	110.1 (3)	N3—C7—C8	110.3 (3)
C27—N5—C25	117.8 (3)	N3—C7—H7A	109.6
C27—N5—C24	116.5 (3)	C8—C7—H7A	109.6
C25—N5—C24	110.9 (3)	N3—C7—H7B	109.6
C23—N6—C26	112.2 (3)	C8—C7—H7B	109.6
C23—N6—H6A	109.2	H7A—C7—H7B	108.1
C26—N6—H6A	109.2	C11—C16—C15	120.8 (4)
C23—N6—H6B	109.2	C11—C16—H16	119.6
C26—N6—H6B	109.2	C15—C16—H16	119.6
H6A—N6—H6B	107.9	C14—C15—C16	120.3 (4)
O1—C1—N2	121.5 (4)	C14—C15—H15	119.8
O1—C1—N1	120.3 (4)	C16—C15—H15	119.8
N2—C1—N1	118.2 (4)	N6—C26—C25	109.6 (3)
O3—C18—N7	119.1 (4)	N6—C26—H26A	109.8
O3—C18—C19	125.1 (4)	C25—C26—H26A	109.8
N7—C18—C19	115.8 (3)	N6—C26—H26B	109.8
O4—C17—N8	121.8 (4)	C25—C26—H26B	109.8
O4—C17—N7	120.4 (4)	H26A—C26—H26B	108.2
N8—C17—N7	117.8 (4)	C13—C12—C11	120.0 (4)
N2—C4—C3	128.3 (4)	C13—C12—H12	120.0
N2—C4—Cl1	112.1 (3)	C11—C12—H12	120.0
C3—C4—Cl1	119.5 (3)	N4—C8—C7	110.1 (3)
O2—C2—N1	119.5 (4)	N4—C8—H8A	109.6
O2—C2—C3	124.5 (4)	C7—C8—H8A	109.6
N1—C2—C3	116.1 (3)	N4—C8—H8B	109.6
N8—C20—C19	129.3 (4)	C7—C8—H8B	109.6
N8—C20—Cl2	111.7 (3)	H8A—C8—H8B	108.2
C19—C20—Cl2	119.0 (3)	C31—C32—C27	121.1 (4)
C16—C11—C12	118.5 (4)	C31—C32—H32	119.5
C16—C11—N4	122.4 (4)	C27—C32—H32	119.5
C12—C11—N4	118.9 (4)	N5—C24—C23	110.1 (3)
N4—C9—C10	109.9 (4)	N5—C24—H24A	109.6
N4—C9—H9A	109.7	C23—C24—H24A	109.6
C10—C9—H9A	109.7	N5—C24—H24B	109.6
N4—C9—H9B	109.7	C23—C24—H24B	109.6
C10—C9—H9B	109.7	H24A—C24—H24B	108.1
H9A—C9—H9B	108.2	C30—C29—C28	120.1 (5)
C28—C27—C32	117.7 (4)	C30—C29—H29	120.0
C28—C27—N5	123.4 (4)	C28—C29—H29	120.0
C32—C27—N5	118.8 (4)	C32—C31—C30	120.7 (5)
C4—C3—C2	115.0 (4)	C32—C31—H31	119.6
C4—C3—C5	124.6 (4)	C30—C31—H31	119.6
C2—C3—C5	120.4 (3)	C14—C13—C12	121.3 (4)
N5—C25—C26	109.5 (4)	C14—C13—H13	119.3
N5—C25—H25A	109.8	C12—C13—H13	119.3
C26—C25—H25A	109.8	C21—C22—H22A	109.5
N5—C25—H25B	109.8	C21—C22—H22B	109.5
C26—C25—H25B	109.8	H22A—C22—H22B	109.5
H25A—C25—H25B	108.2	C21—C22—H22C	109.5
C20—C19—C18	114.5 (4)	H22A—C22—H22C	109.5
C20—C19—C21	124.4 (4)	H22B—C22—H22C	109.5
C18—C19—C21	121.1 (4)	C13—C14—C15	119.0 (4)
N6—C23—C24	110.4 (4)	C13—C14—H14	120.5
N6—C23—H23A	109.6	C15—C14—H14	120.5
C24—C23—H23A	109.6	C29—C30—C31	119.4 (4)
N6—C23—H23B	109.6	C29—C30—H30	120.3
C24—C23—H23B	109.6	C31—C30—H30	120.3
H23A—C23—H23B	108.1	C5—C6—H6C	109.5
C19—C21—C22	113.2 (4)	C5—C6—H6D	109.5
C19—C21—H21A	108.9	H6C—C6—H6D	109.5
C22—C21—H21A	108.9	C5—C6—H6E	109.5
C19—C21—H21B	108.9	H6C—C6—H6E	109.5
C22—C21—H21B	108.9	H6D—C6—H6E	109.5
C4—N2—C1—O1	179.0 (4)	N8—C20—C19—C21	−179.6 (4)
C4—N2—C1—N1	−0.6 (6)	Cl2—C20—C19—C21	2.8 (6)
C2—N1—C1—O1	−178.9 (4)	O3—C18—C19—C20	178.5 (4)
C2—N1—C1—N2	0.7 (6)	N7—C18—C19—C20	−1.4 (6)
C17—N7—C18—O3	−179.1 (4)	O3—C18—C19—C21	−0.9 (7)
C17—N7—C18—C19	0.9 (6)	N7—C18—C19—C21	179.2 (4)
C20—N8—C17—O4	179.6 (4)	C26—N6—C23—C24	−53.9 (5)
C20—N8—C17—N7	−0.8 (6)	C20—C19—C21—C22	76.2 (6)
C18—N7—C17—O4	179.9 (4)	C18—C19—C21—C22	−104.4 (5)
C18—N7—C17—N8	0.3 (6)	C32—C27—C28—C29	−1.8 (6)
C1—N2—C4—C3	1.1 (7)	N5—C27—C28—C29	173.5 (4)
C1—N2—C4—Cl1	−177.7 (3)	C7—N3—C10—C9	−54.1 (4)
C1—N1—C2—O2	179.0 (4)	N4—C9—C10—N3	56.9 (4)
C1—N1—C2—C3	−1.0 (6)	C4—C3—C5—C6	84.3 (5)
C17—N8—C20—C19	0.1 (7)	C2—C3—C5—C6	−92.5 (5)
C17—N8—C20—Cl2	177.9 (3)	C10—N3—C7—C8	53.7 (4)
C9—N4—C11—C16	8.8 (6)	C12—C11—C16—C15	1.2 (6)
C8—N4—C11—C16	−124.1 (4)	N4—C11—C16—C15	−174.7 (4)
C9—N4—C11—C12	−167.1 (4)	C11—C16—C15—C14	−0.7 (7)
C8—N4—C11—C12	60.0 (5)	C23—N6—C26—C25	54.9 (5)
C11—N4—C9—C10	164.1 (3)	N5—C25—C26—N6	−58.0 (4)
C8—N4—C9—C10	−60.6 (4)	C16—C11—C12—C13	−0.4 (6)
C25—N5—C27—C28	−13.7 (6)	N4—C11—C12—C13	175.6 (4)
C24—N5—C27—C28	121.7 (4)	C11—N4—C8—C7	−163.1 (4)
C25—N5—C27—C32	161.5 (4)	C9—N4—C8—C7	60.6 (4)
C24—N5—C27—C32	−63.1 (5)	N3—C7—C8—N4	−56.5 (4)
N2—C4—C3—C2	−1.4 (7)	C28—C27—C32—C31	1.5 (6)
Cl1—C4—C3—C2	177.3 (3)	N5—C27—C32—C31	−174.0 (4)
N2—C4—C3—C5	−178.3 (4)	C27—N5—C24—C23	161.1 (4)
Cl1—C4—C3—C5	0.4 (6)	C25—N5—C24—C23	−60.5 (5)
O2—C2—C3—C4	−178.8 (4)	N6—C23—C24—N5	55.5 (4)
N1—C2—C3—C4	1.2 (6)	C27—C28—C29—C30	1.2 (7)
O2—C2—C3—C5	−1.7 (6)	C27—C32—C31—C30	−0.6 (7)
N1—C2—C3—C5	178.3 (4)	C11—C12—C13—C14	−0.8 (7)
C27—N5—C25—C26	−160.5 (3)	C12—C13—C14—C15	1.3 (7)
C24—N5—C25—C26	61.7 (4)	C16—C15—C14—C13	−0.5 (7)
N8—C20—C19—C18	1.1 (7)	C28—C29—C30—C31	−0.3 (7)
Cl2—C20—C19—C18	−176.5 (3)	C32—C31—C30—C29	0.0 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.00	2.859 (4)	173
N3—H3A···O1^ii	0.89	2.83	3.465 (4)	129
N6—H6A···O4^iii	0.89	1.81	2.681 (5)	165
N7—H7···O3^iv	0.86	2.02	2.873 (4)	174
N3—H3A···N2^ii	0.89	1.92	2.808 (4)	174
N6—H6B···N8^v	0.89	1.92	2.798 (5)	169
C10—H10B···O2^vi	0.97	2.46	3.355 (5)	154
C26—H26A···O3^vii	0.97	2.58	3.444 (5)	147
C16—H16···Cl2^viii	0.93	2.80	3.462 (4)	129

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

(II) 4-Phenylpiperazin-1-ium 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide

Crystal data

C10H15N2^+·C7H8ClN2O2^−	F(000) = 1488
Mr = 350.84	Dx = 1.318 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.5418 Å
a = 20.5012 (3) Å	Cell parameters from 6927 reflections
b = 7.4565 (1) Å	θ = 3.8–70.0°
c = 23.1414 (3) Å	µ = 2.05 mm^−1
β = 90.639 (1)°	T = 101 K
V = 3537.34 (8) Å^3	Prism, colourless
Z = 8	0.34 × 0.13 × 0.09 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer	2926 reflections with I > 2σ(I)
Detector resolution: 10.2673 pixels mm^-1	Rint = 0.069
ω scans	θmax = 70.6°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −24→25
Tmin = 0.760, Tmax = 0.828	k = −9→7
13174 measured reflections	l = −27→28
3396 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 3.6877P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3346 reflections	Δρmax = 0.55 e Å^−3
217 parameters	Δρmin = −0.56 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.43825 (2)	0.80800 (7)	0.38729 (2)	0.03420 (17)
O1	0.42855 (6)	1.32956 (18)	0.26398 (6)	0.0286 (3)
O2	0.23184 (6)	1.07264 (19)	0.29852 (6)	0.0288 (3)
N3	0.33106 (7)	1.1946 (2)	0.28125 (6)	0.0227 (3)
H3	0.3124	1.2711	0.2587	0.027*
N4	0.42771 (7)	1.0889 (2)	0.32365 (6)	0.0228 (3)
N2	0.56397 (7)	1.1049 (2)	0.31180 (6)	0.0246 (3)
H3N	0.5734	1.0238	0.2849	0.029*
H2N	0.5208	1.1087	0.3152	0.029*
C11	0.39765 (9)	1.2092 (2)	0.28906 (7)	0.0228 (4)
N1	0.60877 (7)	1.3622 (2)	0.39443 (6)	0.0230 (3)
C2	0.58171 (9)	1.1911 (2)	0.41332 (8)	0.0237 (4)
H2A	0.5352	1.2036	0.4195	0.028*
H2B	0.6020	1.1556	0.4496	0.028*
C4	0.58796 (10)	1.2834 (3)	0.29310 (8)	0.0271 (4)
H4A	0.5649	1.3201	0.2582	0.032*
H4B	0.6341	1.2760	0.2845	0.032*
C14	0.39071 (9)	0.9583 (2)	0.34646 (7)	0.0236 (4)
C12	0.29194 (9)	1.0666 (3)	0.30679 (7)	0.0232 (4)
C6	0.58544 (9)	1.4868 (3)	0.49109 (8)	0.0273 (4)
H6	0.5581	1.3906	0.4992	0.033*
C13	0.32496 (9)	0.9324 (2)	0.34113 (7)	0.0231 (4)
C3	0.59378 (9)	1.0490 (3)	0.36799 (8)	0.0245 (4)
H3A	0.6403	1.0318	0.3634	0.029*
H3B	0.5750	0.9361	0.3802	0.029*
C10	0.65511 (9)	1.6458 (3)	0.42609 (8)	0.0272 (4)
H10	0.6749	1.6571	0.3903	0.033*
C15	0.28407 (10)	0.7802 (3)	0.36508 (8)	0.0286 (4)
H15	0.2393	0.8063	0.3523	0.034*
C5	0.61534 (9)	1.4980 (2)	0.43717 (8)	0.0224 (4)
C8	0.63624 (10)	1.7627 (3)	0.52142 (9)	0.0341 (5)
H8	0.6436	1.8500	0.5494	0.041*
C1	0.57729 (9)	1.4207 (3)	0.34016 (7)	0.0249 (4)
H1A	0.5953	1.5352	0.3284	0.030*
H1B	0.5309	1.4365	0.3462	0.030*
C7	0.59623 (10)	1.6182 (3)	0.53262 (8)	0.0332 (5)
H7	0.5763	1.6088	0.5684	0.040*
C9	0.66531 (10)	1.7757 (3)	0.46790 (9)	0.0320 (5)
H9	0.6921	1.8731	0.4599	0.038*
C16	0.28114 (10)	0.7739 (3)	0.43025 (8)	0.0310 (4)
H16A	0.2708	0.8909	0.4448	0.047*
H16B	0.2481	0.6902	0.4418	0.047*
H16C	0.3227	0.7365	0.4456	0.047*
C17	0.30027 (12)	0.6004 (3)	0.33815 (9)	0.0394 (5)
H17A	0.3015	0.6125	0.2969	0.059*
H17B	0.3421	0.5605	0.3522	0.059*
H17C	0.2675	0.5143	0.3483	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0307 (3)	0.0306 (3)	0.0413 (3)	0.00185 (19)	0.0001 (2)	0.0141 (2)
O1	0.0225 (7)	0.0278 (7)	0.0355 (7)	−0.0043 (6)	0.0020 (5)	0.0107 (6)
O2	0.0210 (6)	0.0341 (8)	0.0313 (7)	−0.0042 (6)	0.0017 (5)	0.0053 (6)
N3	0.0210 (7)	0.0233 (8)	0.0238 (7)	−0.0013 (6)	0.0012 (6)	0.0032 (6)
N4	0.0233 (7)	0.0211 (8)	0.0239 (7)	0.0003 (6)	0.0022 (6)	0.0025 (6)
N2	0.0227 (7)	0.0256 (8)	0.0255 (7)	0.0009 (7)	0.0023 (6)	−0.0055 (6)
C11	0.0238 (9)	0.0216 (9)	0.0231 (8)	−0.0010 (7)	0.0033 (7)	−0.0021 (7)
N1	0.0261 (8)	0.0203 (8)	0.0225 (7)	0.0005 (6)	0.0007 (6)	0.0002 (6)
C2	0.0254 (9)	0.0221 (9)	0.0235 (8)	0.0009 (7)	0.0020 (7)	0.0010 (7)
C4	0.0302 (10)	0.0284 (10)	0.0226 (9)	−0.0025 (8)	0.0023 (7)	−0.0003 (8)
C14	0.0295 (9)	0.0207 (9)	0.0206 (8)	0.0023 (8)	0.0024 (7)	−0.0001 (7)
C12	0.0255 (9)	0.0244 (9)	0.0198 (8)	−0.0036 (8)	0.0043 (7)	−0.0030 (7)
C6	0.0300 (10)	0.0248 (10)	0.0273 (9)	−0.0002 (8)	0.0003 (8)	−0.0004 (8)
C13	0.0287 (9)	0.0209 (9)	0.0198 (8)	−0.0031 (8)	0.0042 (7)	−0.0022 (7)
C3	0.0231 (9)	0.0221 (9)	0.0284 (9)	0.0017 (7)	0.0017 (7)	−0.0005 (7)
C10	0.0241 (9)	0.0254 (10)	0.0322 (10)	0.0019 (8)	0.0017 (7)	−0.0005 (8)
C15	0.0317 (10)	0.0262 (10)	0.0279 (9)	−0.0059 (8)	0.0039 (8)	0.0007 (8)
C5	0.0201 (8)	0.0211 (9)	0.0260 (9)	0.0053 (7)	−0.0028 (7)	−0.0015 (7)
C8	0.0376 (11)	0.0290 (11)	0.0354 (10)	0.0050 (9)	−0.0084 (9)	−0.0106 (9)
C1	0.0284 (9)	0.0236 (9)	0.0227 (8)	0.0002 (8)	0.0006 (7)	0.0016 (7)
C7	0.0385 (11)	0.0350 (11)	0.0260 (9)	0.0066 (9)	0.0012 (8)	−0.0053 (8)
C9	0.0273 (10)	0.0241 (10)	0.0445 (11)	−0.0005 (8)	−0.0056 (8)	−0.0034 (9)
C16	0.0318 (10)	0.0306 (11)	0.0309 (10)	−0.0049 (9)	0.0092 (8)	0.0003 (8)
C17	0.0492 (13)	0.0299 (11)	0.0396 (11)	−0.0130 (10)	0.0139 (10)	−0.0048 (9)

Geometric parameters (Å, º)

Cl1—C14	1.7544 (18)	C6—C7	1.389 (3)
O1—C11	1.246 (2)	C6—C5	1.399 (3)
O2—C12	1.246 (2)	C6—H6	0.9300
N3—C11	1.379 (2)	C13—C15	1.519 (3)
N3—C12	1.383 (2)	C3—H3A	0.9700
N3—H3	0.8600	C3—H3B	0.9700
N4—N4	0.000 (5)	C10—C9	1.383 (3)
N4—C14	1.346 (2)	C10—C5	1.397 (3)
N4—C11	1.347 (2)	C10—H10	0.9300
N2—C4	1.485 (2)	C15—C16	1.511 (3)
N2—C3	1.490 (2)	C15—C17	1.517 (3)
N2—H3N	0.8900	C15—H15	0.9800
N2—H2N	0.8900	C8—C7	1.380 (3)
C11—N4	1.347 (2)	C8—C9	1.384 (3)
N1—C5	1.421 (2)	C8—H8	0.9300
N1—C2	1.460 (2)	C1—H1A	0.9700
N1—C1	1.472 (2)	C1—H1B	0.9700
C2—C3	1.513 (2)	C7—H7	0.9300
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C16—H16A	0.9600
C4—C1	1.512 (3)	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600
C4—H4B	0.9700	C17—H17A	0.9600
C14—N4	1.346 (2)	C17—H17B	0.9600
C14—C13	1.366 (3)	C17—H17C	0.9600
C12—C13	1.442 (3)
C11—N3—C12	125.17 (16)	C12—C13—C15	117.51 (16)
C11—N3—H3	117.4	N2—C3—C2	109.92 (15)
C12—N3—H3	117.4	N2—C3—H3A	109.7
N4—N4—C14	0 (10)	C2—C3—H3A	109.7
N4—N4—C11	0 (10)	N2—C3—H3B	109.7
C14—N4—C11	117.31 (15)	C2—C3—H3B	109.7
C4—N2—C3	111.77 (14)	H3A—C3—H3B	108.2
C4—N2—H3N	109.3	C9—C10—C5	120.54 (18)
C3—N2—H3N	109.3	C9—C10—H10	119.7
C4—N2—H2N	109.3	C5—C10—H10	119.7
C3—N2—H2N	109.3	C16—C15—C17	113.20 (18)
H3N—N2—H2N	107.9	C16—C15—C13	114.57 (16)
O1—C11—N4	121.67 (16)	C17—C15—C13	112.72 (16)
O1—C11—N4	121.67 (16)	C16—C15—H15	105.1
N4—C11—N4	0.00 (14)	C17—C15—H15	105.1
O1—C11—N3	120.23 (17)	C13—C15—H15	105.1
N4—C11—N3	118.10 (16)	C10—C5—C6	118.26 (17)
N4—C11—N3	118.10 (16)	C10—C5—N1	119.06 (16)
C5—N1—C2	116.59 (14)	C6—C5—N1	122.64 (17)
C5—N1—C1	114.83 (15)	C7—C8—C9	119.04 (19)
C2—N1—C1	110.50 (14)	C7—C8—H8	120.5
N1—C2—C3	109.78 (14)	C9—C8—H8	120.5
N1—C2—H2A	109.7	N1—C1—C4	110.37 (15)
C3—C2—H2A	109.7	N1—C1—H1A	109.6
N1—C2—H2B	109.7	C4—C1—H1A	109.6
C3—C2—H2B	109.7	N1—C1—H1B	109.6
H2A—C2—H2B	108.2	C4—C1—H1B	109.6
N2—C4—C1	110.25 (15)	H1A—C1—H1B	108.1
N2—C4—H4A	109.6	C8—C7—C6	120.75 (19)
C1—C4—H4A	109.6	C8—C7—H7	119.6
N2—C4—H4B	109.6	C6—C7—H7	119.6
C1—C4—H4B	109.6	C10—C9—C8	120.9 (2)
H4A—C4—H4B	108.1	C10—C9—H9	119.5
N4—C14—N4	0.00 (17)	C8—C9—H9	119.5
N4—C14—C13	128.81 (17)	C15—C16—H16A	109.5
N4—C14—C13	128.81 (17)	C15—C16—H16B	109.5
N4—C14—Cl1	111.18 (13)	H16A—C16—H16B	109.5
N4—C14—Cl1	111.18 (13)	C15—C16—H16C	109.5
C13—C14—Cl1	120.01 (14)	H16A—C16—H16C	109.5
O2—C12—N3	119.11 (17)	H16B—C16—H16C	109.5
O2—C12—C13	124.56 (17)	C15—C17—H17A	109.5
N3—C12—C13	116.32 (16)	C15—C17—H17B	109.5
C7—C6—C5	120.48 (19)	H17A—C17—H17B	109.5
C7—C6—H6	119.8	C15—C17—H17C	109.5
C5—C6—H6	119.8	H17A—C17—H17C	109.5
C14—C13—C12	114.11 (16)	H17B—C17—H17C	109.5
C14—C13—C15	128.36 (17)
N4—N4—C11—O1	0.0 (5)	N3—C12—C13—C14	4.0 (2)
C14—N4—C11—O1	−176.64 (16)	O2—C12—C13—C15	4.8 (3)
C14—N4—C11—N4	0 (100)	N3—C12—C13—C15	−174.41 (15)
N4—N4—C11—N3	0.0 (4)	C4—N2—C3—C2	55.49 (19)
C14—N4—C11—N3	2.5 (2)	N1—C2—C3—N2	−58.11 (19)
C12—N3—C11—O1	179.96 (16)	C14—C13—C15—C16	65.7 (3)
C12—N3—C11—N4	0.8 (3)	C12—C13—C15—C16	−116.20 (19)
C12—N3—C11—N4	0.8 (3)	C14—C13—C15—C17	−65.7 (3)
C5—N1—C2—C3	−165.61 (15)	C12—C13—C15—C17	112.4 (2)
C1—N1—C2—C3	60.88 (19)	C9—C10—C5—C6	1.1 (3)
C3—N2—C4—C1	−54.5 (2)	C9—C10—C5—N1	−176.58 (17)
C11—N4—C14—N4	0 (100)	C7—C6—C5—C10	−1.1 (3)
N4—N4—C14—C13	0.0 (3)	C7—C6—C5—N1	176.42 (17)
C11—N4—C14—C13	−2.5 (3)	C2—N1—C5—C10	164.11 (16)
N4—N4—C14—Cl1	0.0 (3)	C1—N1—C5—C10	−64.4 (2)
C11—N4—C14—Cl1	177.09 (13)	C2—N1—C5—C6	−13.4 (2)
C11—N3—C12—O2	176.56 (16)	C1—N1—C5—C6	118.11 (19)
C11—N3—C12—C13	−4.2 (3)	C5—N1—C1—C4	165.63 (15)
N4—C14—C13—C12	−0.9 (3)	C2—N1—C1—C4	−59.98 (19)
N4—C14—C13—C12	−0.9 (3)	N2—C4—C1—N1	56.0 (2)
Cl1—C14—C13—C12	179.55 (12)	C9—C8—C7—C6	0.4 (3)
N4—C14—C13—C15	177.27 (17)	C5—C6—C7—C8	0.4 (3)
N4—C14—C13—C15	177.27 (17)	C5—C10—C9—C8	−0.3 (3)
Cl1—C14—C13—C15	−2.3 (3)	C7—C8—C9—C10	−0.5 (3)
O2—C12—C13—C14	−176.82 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N4	0.89	1.93	2.813 (2)	174
N2—H3N···O1^i	0.89	1.84	2.705 (2)	164
N3—H3···O2^ii	0.86	1.98	2.834 (2)	174
C3—H3A···O2^iii	0.97	2.54	3.394 (2)	147

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1/2, −y+5/2, −z+1/2; (iii) x+1/2, −y+2, z.