The first coordination complex of (5R,6R,7S)-5-(furan-2-yl)-7-phenyl-4,5,6,7-tetra­hydro-[1,2,4]triazolo[1,5-a]pyrimidin-6-amine with zinc(II) acetate-chloride

The first coordination complex with (5R,6R,7S)-5-(furan-2-yl)-7-phenyl-4,5,6,7-tetra­hydro-[1,2,4]triazolo[1,5-α]pyrimidin-6-amino as a bridged ligand coordinating two zinc atoms has been synthesized and studied.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.042
• wR factor = 0.102
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.628 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         10 Report
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        19% Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1_1           106.1 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         23 Note
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         90 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   3 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.

   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

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

catena-Poly[[[acetatochloridozinc(II)]-µ-(5R,6R,7S)-5-(furan-2-yl)-7-phenyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidin-6-amine] monohydrate]

Crystal data

[Zn(C2H3O2)Cl(C15H15N5O)]·H2O	F(000) = 944
Mr = 459.20	Dx = 1.529 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.6267 (4) Å	Cell parameters from 3540 reflections
b = 12.8015 (5) Å	θ = 3.1–29.5°
c = 15.1646 (7) Å	µ = 1.40 mm^−1
β = 104.788 (4)°	T = 293 K
V = 1994.63 (15) Å^3	Needle, colourless
Z = 4	0.2 × 0.2 × 0.1 mm

Data collection

Xcalibur, Sapphire3 diffractometer	3174 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.042
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	h = −13→13
Tmin = 0.930, Tmax = 1.000	k = −16→16
15201 measured reflections	l = −19→19
4572 independent reflections

Refinement

Refinement on F^2	90 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.1268P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4572 reflections	Δρmax = 0.36 e Å^−3
291 parameters	Δρmin = −0.32 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.42716 (3)	0.16102 (3)	0.59755 (2)	0.03857 (12)
Cl1	0.62402 (7)	0.20953 (6)	0.58000 (6)	0.0524 (2)
O1S	0.4892 (2)	0.14368 (17)	0.36476 (14)	0.0552 (6)
H1SA	0.416347	0.120957	0.389178	0.083*
H1SB	0.562247	0.163167	0.416278	0.083*
O2	0.32493 (19)	0.10659 (17)	0.48190 (13)	0.0481 (5)
O3	0.18743 (19)	0.07023 (18)	0.56429 (15)	0.0545 (6)
N1	0.5043 (2)	0.42425 (18)	0.62954 (16)	0.0437 (6)
H1	0.560504	0.381973	0.617396	0.052*
N2	0.3175 (2)	0.44947 (17)	0.68186 (15)	0.0342 (5)
N3	0.2161 (2)	0.39097 (19)	0.69900 (16)	0.0424 (6)
N4	0.3523 (2)	0.28948 (17)	0.64306 (15)	0.0358 (5)
N5	0.5586 (2)	0.55569 (17)	0.79892 (14)	0.0352 (5)
H5A	0.638491	0.541918	0.793789	0.042*
H5B	0.526184	0.496510	0.814732	0.042*
C1	0.3340 (2)	0.5612 (2)	0.70008 (18)	0.0350 (6)
H1A	0.316410	0.574588	0.759441	0.042*
C2	0.4782 (2)	0.5873 (2)	0.70857 (17)	0.0340 (6)
H2	0.485507	0.663307	0.703691	0.041*
C3	0.5248 (3)	0.5371 (2)	0.62890 (19)	0.0365 (6)
H3	0.472603	0.565499	0.571084	0.044*
C4	0.3965 (2)	0.3877 (2)	0.64934 (17)	0.0328 (6)
C5	0.2433 (3)	0.2978 (2)	0.67508 (19)	0.0403 (6)
H5	0.191826	0.240239	0.679448	0.048*
C6	0.2415 (3)	0.6275 (2)	0.6302 (2)	0.0389 (6)
C7	0.2274 (3)	0.7316 (2)	0.6495 (2)	0.0541 (8)
H7	0.273434	0.758626	0.705375	0.065*
C8	0.1466 (3)	0.7960 (3)	0.5875 (3)	0.0693 (11)
H8	0.139303	0.866309	0.600944	0.083*
C9	0.0773 (3)	0.7563 (3)	0.5065 (3)	0.0681 (10)
H9	0.020910	0.799302	0.465039	0.082*
C10	0.0898 (3)	0.6544 (3)	0.4856 (3)	0.0641 (10)
H10	0.042548	0.628125	0.429733	0.077*
C11	0.1729 (3)	0.5892 (3)	0.5472 (2)	0.0510 (8)
H11	0.182172	0.519689	0.532211	0.061*
O1_1	0.6872 (5)	0.6493 (4)	0.5947 (4)	0.0578 (14)	0.707 (11)
C12_1	0.6648 (3)	0.5593 (2)	0.63613 (19)	0.0404 (6)	0.707 (11)
C13_1	0.7773 (9)	0.5100 (9)	0.6723 (8)	0.064 (2)	0.707 (11)
H13_1	0.786583	0.444450	0.699558	0.076*	0.707 (11)
C14_1	0.8815 (6)	0.5769 (7)	0.6613 (6)	0.067 (2)	0.707 (11)
H14_1	0.970497	0.565320	0.682355	0.081*	0.707 (11)
C15_1	0.8216 (7)	0.6599 (5)	0.6139 (5)	0.0609 (17)	0.707 (11)
H15_1	0.864388	0.716553	0.596380	0.073*	0.707 (11)
O1_2	0.7572 (13)	0.4952 (13)	0.6906 (12)	0.054 (3)	0.293 (11)
C12_2	0.6648 (3)	0.5593 (2)	0.63613 (19)	0.0404 (6)	0.293 (11)
C13_2	0.7307 (17)	0.6428 (15)	0.6144 (16)	0.055 (3)	0.293 (11)
H13_2	0.693906	0.703607	0.585317	0.066*	0.293 (11)
C14_2	0.8683 (14)	0.6197 (14)	0.6447 (13)	0.055 (3)	0.293 (11)
H14_2	0.935927	0.660277	0.634767	0.065*	0.293 (11)
C15_2	0.8800 (12)	0.5283 (14)	0.6901 (10)	0.055 (3)	0.293 (11)
H15_2	0.957438	0.493801	0.716452	0.066*	0.293 (11)
C16_2	0.2172 (3)	0.0672 (2)	0.4915 (2)	0.0410 (7)
C17_2	0.1314 (3)	0.0175 (3)	0.4078 (2)	0.0573 (8)
H17A_2	0.124694	0.062911	0.356446	0.086*
H17B_2	0.046435	0.005959	0.417039	0.086*
H17C_2	0.168324	−0.048027	0.396537	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0440 (2)	0.03285 (19)	0.0390 (2)	−0.00017 (14)	0.01079 (14)	0.00118 (14)
Cl1	0.0451 (4)	0.0508 (5)	0.0657 (5)	−0.0013 (3)	0.0220 (4)	−0.0036 (4)
O1S	0.0621 (14)	0.0589 (15)	0.0466 (13)	−0.0016 (11)	0.0171 (11)	−0.0110 (10)
O2	0.0505 (12)	0.0500 (13)	0.0450 (12)	−0.0136 (10)	0.0144 (10)	−0.0036 (10)
O3	0.0477 (12)	0.0654 (15)	0.0517 (13)	−0.0037 (11)	0.0148 (10)	−0.0044 (11)
N1	0.0453 (13)	0.0337 (13)	0.0596 (16)	−0.0047 (11)	0.0275 (12)	−0.0088 (12)
N2	0.0324 (11)	0.0294 (12)	0.0413 (13)	−0.0018 (9)	0.0105 (10)	0.0006 (10)
N3	0.0356 (12)	0.0390 (14)	0.0541 (15)	−0.0041 (11)	0.0143 (11)	0.0018 (12)
N4	0.0386 (12)	0.0295 (12)	0.0387 (13)	−0.0032 (10)	0.0088 (10)	−0.0003 (10)
N5	0.0370 (12)	0.0307 (12)	0.0380 (13)	0.0005 (10)	0.0100 (10)	−0.0021 (10)
C1	0.0357 (14)	0.0313 (14)	0.0393 (15)	0.0032 (11)	0.0119 (12)	−0.0044 (12)
C2	0.0374 (14)	0.0258 (13)	0.0375 (15)	−0.0002 (11)	0.0075 (11)	0.0006 (11)
C3	0.0415 (15)	0.0324 (14)	0.0366 (15)	−0.0018 (12)	0.0121 (12)	0.0001 (12)
C4	0.0368 (14)	0.0303 (14)	0.0311 (14)	−0.0015 (11)	0.0081 (11)	0.0007 (11)
C5	0.0369 (14)	0.0369 (15)	0.0475 (17)	−0.0056 (12)	0.0118 (13)	0.0003 (13)
C6	0.0320 (14)	0.0336 (15)	0.0517 (18)	0.0024 (12)	0.0119 (13)	0.0030 (13)
C7	0.0497 (18)	0.0392 (18)	0.070 (2)	0.0094 (15)	0.0087 (16)	−0.0005 (16)
C8	0.055 (2)	0.043 (2)	0.108 (3)	0.0121 (17)	0.018 (2)	0.009 (2)
C9	0.0477 (19)	0.069 (3)	0.087 (3)	0.0123 (19)	0.015 (2)	0.028 (2)
C10	0.0494 (19)	0.073 (3)	0.064 (2)	0.0101 (18)	0.0042 (17)	0.013 (2)
C11	0.0472 (17)	0.0461 (18)	0.055 (2)	0.0086 (15)	0.0051 (15)	0.0027 (16)
O1_1	0.046 (2)	0.047 (2)	0.082 (3)	−0.011 (2)	0.019 (2)	0.016 (2)
C12_1	0.0424 (14)	0.0383 (15)	0.0449 (16)	−0.0020 (12)	0.0188 (13)	0.0012 (12)
C13_1	0.054 (4)	0.065 (4)	0.078 (5)	0.005 (3)	0.026 (3)	0.019 (3)
C14_1	0.055 (3)	0.065 (5)	0.085 (5)	0.003 (3)	0.023 (3)	0.008 (4)
C15_1	0.045 (3)	0.053 (3)	0.090 (4)	−0.014 (3)	0.028 (3)	0.006 (3)
O1_2	0.038 (5)	0.066 (5)	0.060 (6)	0.002 (4)	0.016 (4)	0.022 (4)
C12_2	0.0424 (14)	0.0383 (15)	0.0449 (16)	−0.0020 (12)	0.0188 (13)	0.0012 (12)
C13_2	0.044 (6)	0.048 (6)	0.064 (6)	0.000 (5)	−0.003 (6)	0.014 (5)
C14_2	0.041 (5)	0.061 (8)	0.061 (7)	0.000 (5)	0.010 (5)	0.019 (6)
C15_2	0.034 (5)	0.069 (7)	0.061 (6)	0.004 (5)	0.009 (5)	0.017 (5)
C16_2	0.0451 (16)	0.0306 (15)	0.0456 (18)	0.0043 (12)	0.0082 (14)	0.0021 (13)
C17_2	0.0482 (17)	0.059 (2)	0.060 (2)	−0.0102 (16)	0.0043 (15)	−0.0079 (17)

Geometric parameters (Å, º)

Zn1—Cl1	2.2621 (8)	C6—C11	1.374 (4)
Zn1—O2	1.9413 (19)	C7—H7	0.9300
Zn1—N4	2.023 (2)	C7—C8	1.374 (5)
Zn1—N5^i	2.046 (2)	C8—H8	0.9300
O1S—H1SA	0.9832	C8—C9	1.360 (5)
O1S—H1SB	0.9829	C9—H9	0.9300
O2—C16_2	1.293 (3)	C9—C10	1.357 (5)
O3—C16_2	1.224 (3)	C10—H10	0.9300
N1—H1	0.8600	C10—C11	1.388 (4)
N1—C3	1.461 (3)	C11—H11	0.9300
N1—C4	1.340 (3)	O1_1—C12_1	1.362 (5)
N2—N3	1.390 (3)	O1_1—C15_1	1.389 (6)
N2—C1	1.459 (3)	C12_1—C13_1	1.338 (10)
N2—C4	1.336 (3)	C13_1—H13_1	0.9300
N3—C5	1.301 (4)	C13_1—C14_1	1.442 (10)
N4—C4	1.337 (3)	C14_1—H14_1	0.9300
N4—C5	1.370 (3)	C14_1—C15_1	1.348 (8)
N5—H5A	0.8900	C15_1—H15_1	0.9300
N5—H5B	0.8900	O1_2—C12_2	1.380 (13)
N5—C2	1.474 (3)	O1_2—C15_2	1.374 (14)
C1—H1A	0.9800	C12_2—C13_2	1.364 (18)
C1—C2	1.542 (3)	C13_2—H13_2	0.9300
C1—C6	1.509 (4)	C13_2—C14_2	1.447 (15)
C2—H2	0.9800	C14_2—H14_2	0.9300
C2—C3	1.557 (4)	C14_2—C15_2	1.346 (15)
C3—H3	0.9800	C15_2—H15_2	0.9300
C3—C12_1	1.491 (4)	C16_2—C17_2	1.501 (4)
C3—C12_2	1.491 (4)	C17_2—H17A_2	0.9600
C5—H5	0.9300	C17_2—H17B_2	0.9600
C6—C7	1.381 (4)	C17_2—H17C_2	0.9600
O2—Zn1—Cl1	108.26 (6)	C11—C6—C7	118.5 (3)
O2—Zn1—N4	114.95 (9)	C6—C7—H7	119.4
O2—Zn1—N5^i	111.81 (9)	C8—C7—C6	121.1 (3)
N4—Zn1—Cl1	105.83 (6)	C8—C7—H7	119.4
N4—Zn1—N5^i	103.45 (9)	C7—C8—H8	120.2
N5^i—Zn1—Cl1	112.44 (6)	C9—C8—C7	119.6 (4)
H1SA—O1S—H1SB	108.3	C9—C8—H8	120.2
C16_2—O2—Zn1	110.22 (17)	C8—C9—H9	119.7
C3—N1—H1	120.5	C10—C9—C8	120.5 (3)
C4—N1—H1	120.5	C10—C9—H9	119.7
C4—N1—C3	119.0 (2)	C9—C10—H10	119.9
N3—N2—C1	123.6 (2)	C9—C10—C11	120.3 (4)
C4—N2—N3	109.9 (2)	C11—C10—H10	119.9
C4—N2—C1	126.5 (2)	C6—C11—C10	120.0 (3)
C5—N3—N2	101.8 (2)	C6—C11—H11	120.0
C4—N4—Zn1	128.83 (17)	C10—C11—H11	120.0
C4—N4—C5	102.4 (2)	C12_1—O1_1—C15_1	106.1 (4)
C5—N4—Zn1	128.72 (19)	O1_1—C12_1—C3	114.6 (3)
Zn1^ii—N5—H5A	108.2	C13_1—C12_1—C3	135.3 (5)
Zn1^ii—N5—H5B	108.2	C13_1—C12_1—O1_1	110.1 (4)
H5A—N5—H5B	107.3	C12_1—C13_1—H13_1	126.1
C2—N5—Zn1^ii	116.37 (16)	C12_1—C13_1—C14_1	107.7 (7)
C2—N5—H5A	108.2	C14_1—C13_1—H13_1	126.1
C2—N5—H5B	108.2	C13_1—C14_1—H14_1	127.5
N2—C1—H1A	107.7	C15_1—C14_1—C13_1	104.9 (6)
N2—C1—C2	107.3 (2)	C15_1—C14_1—H14_1	127.5
N2—C1—C6	113.1 (2)	O1_1—C15_1—H15_1	124.6
C2—C1—H1A	107.7	C14_1—C15_1—O1_1	110.8 (5)
C6—C1—H1A	107.7	C14_1—C15_1—H15_1	124.6
C6—C1—C2	113.1 (2)	C15_2—O1_2—C12_2	110.2 (9)
N5—C2—C1	110.2 (2)	O1_2—C12_2—C3	118.3 (6)
N5—C2—H2	107.7	C13_2—C12_2—C3	134.1 (8)
N5—C2—C3	112.6 (2)	C13_2—C12_2—O1_2	106.3 (8)
C1—C2—H2	107.7	C12_2—C13_2—H13_2	126.2
C1—C2—C3	110.6 (2)	C12_2—C13_2—C14_2	107.6 (11)
C3—C2—H2	107.7	C14_2—C13_2—H13_2	126.2
N1—C3—C2	109.0 (2)	C13_2—C14_2—H14_2	126.4
N1—C3—H3	108.8	C15_2—C14_2—C13_2	107.1 (12)
N1—C3—C12_1	109.6 (2)	C15_2—C14_2—H14_2	126.4
N1—C3—C12_2	109.6 (2)	O1_2—C15_2—H15_2	126.1
C2—C3—H3	108.8	C14_2—C15_2—O1_2	107.9 (11)
C12_1—C3—C2	111.9 (2)	C14_2—C15_2—H15_2	126.1
C12_1—C3—H3	108.8	O2—C16_2—C17_2	115.7 (3)
C12_2—C3—C2	111.9 (2)	O3—C16_2—O2	122.0 (3)
N2—C4—N1	121.9 (2)	O3—C16_2—C17_2	122.3 (3)
N2—C4—N4	109.9 (2)	C16_2—C17_2—H17A_2	109.5
N4—C4—N1	128.1 (2)	C16_2—C17_2—H17B_2	109.5
N3—C5—N4	116.0 (2)	C16_2—C17_2—H17C_2	109.5
N3—C5—H5	122.0	H17A_2—C17_2—H17B_2	109.5
N4—C5—H5	122.0	H17A_2—C17_2—H17C_2	109.5
C7—C6—C1	118.7 (3)	H17B_2—C17_2—H17C_2	109.5
C11—C6—C1	122.8 (3)
Zn1—O2—C16_2—O3	2.8 (4)	C2—C3—C12_2—O1_2	84.5 (10)
Zn1—O2—C16_2—C17_2	−177.2 (2)	C2—C3—C12_2—C13_2	−80.4 (15)
Zn1—N4—C4—N1	−2.3 (4)	C3—N1—C4—N2	−10.4 (4)
Zn1—N4—C4—N2	179.18 (17)	C3—N1—C4—N4	171.3 (3)
Zn1—N4—C5—N3	−179.08 (19)	C3—C12_1—C13_1—C14_1	−176.4 (5)
Zn1^ii—N5—C2—C1	−85.3 (2)	C3—C12_2—C13_2—C14_2	175.5 (10)
Zn1^ii—N5—C2—C3	150.70 (17)	C4—N1—C3—C2	38.6 (3)
N1—C3—C12_1—O1_1	150.2 (4)	C4—N1—C3—C12_1	161.4 (2)
N1—C3—C12_1—C13_1	−27.6 (9)	C4—N1—C3—C12_2	161.4 (2)
N1—C3—C12_2—O1_2	−36.5 (10)	C4—N2—N3—C5	0.1 (3)
N1—C3—C12_2—C13_2	158.6 (15)	C4—N2—C1—C2	−19.9 (3)
N2—N3—C5—N4	−0.6 (3)	C4—N2—C1—C6	105.5 (3)
N2—C1—C2—N5	−78.2 (2)	C4—N4—C5—N3	0.8 (3)
N2—C1—C2—C3	47.0 (3)	C5—N4—C4—N1	177.8 (3)
N2—C1—C6—C7	166.3 (2)	C5—N4—C4—N2	−0.7 (3)
N2—C1—C6—C11	−15.4 (4)	C6—C1—C2—N5	156.3 (2)
N3—N2—C1—C2	158.2 (2)	C6—C1—C2—C3	−78.5 (3)
N3—N2—C1—C6	−76.3 (3)	C6—C7—C8—C9	1.2 (5)
N3—N2—C4—N1	−178.1 (2)	C7—C6—C11—C10	−1.3 (4)
N3—N2—C4—N4	0.4 (3)	C7—C8—C9—C10	−1.6 (5)
N5—C2—C3—N1	66.3 (3)	C8—C9—C10—C11	0.5 (6)
N5—C2—C3—C12_1	−55.1 (3)	C9—C10—C11—C6	0.9 (5)
N5—C2—C3—C12_2	−55.1 (3)	C11—C6—C7—C8	0.2 (5)
C1—N2—N3—C5	−178.3 (2)	O1_1—C12_1—C13_1—C14_1	5.6 (11)
C1—N2—C4—N1	0.2 (4)	C12_1—O1_1—C15_1—C14_1	3.2 (7)
C1—N2—C4—N4	178.8 (2)	C12_1—C13_1—C14_1—C15_1	−3.5 (11)
C1—C2—C3—N1	−57.5 (3)	C13_1—C14_1—C15_1—O1_1	0.1 (9)
C1—C2—C3—C12_1	−178.9 (2)	C15_1—O1_1—C12_1—C3	176.1 (4)
C1—C2—C3—C12_2	−178.9 (2)	C15_1—O1_1—C12_1—C13_1	−5.5 (8)
C1—C6—C7—C8	178.6 (3)	O1_2—C12_2—C13_2—C14_2	9 (2)
C1—C6—C11—C10	−179.6 (3)	C12_2—O1_2—C15_2—C14_2	7 (2)
C2—C1—C6—C7	−71.5 (3)	C12_2—C13_2—C14_2—C15_2	−5 (2)
C2—C1—C6—C11	106.9 (3)	C13_2—C14_2—C15_2—O1_2	−1 (2)
C2—C3—C12_1—O1_1	−88.7 (4)	C15_2—O1_2—C12_2—C3	−179.0 (10)
C2—C3—C12_1—C13_1	93.4 (9)	C15_2—O1_2—C12_2—C13_2	−10 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1SA···O2	0.98	1.91	2.830 (3)	155
O1S—H1SB···Cl1	0.98	2.47	3.321 (2)	144
N1—H1···Cl1	0.86	2.42	3.198 (2)	151
N5—H5A···O3^ii	0.89	2.48	2.961 (3)	114
N5—H5A···C12_1	0.89	2.49	2.966 (3)	114
N5—H5A···C13_1	0.89	2.67	3.422 (11)	143
N5—H5A···O1_2	0.89	2.33	3.086 (17)	144
N5—H5A···C12_2	0.89	2.49	2.966 (3)	114
N5—H5B···O1S^iii	0.89	2.03	2.904 (3)	169

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