Two Cu^II complexes of 3,4,5-tri­methyl-1H-pyrazole

The crystal structures of two Cu^II complexes of 1-H-3,4,5-tri­methyl­pyrazole, cis-[{CuCl[3,4,5-(CH₃)₃(C₃H₂N₂)]₂}₂(μ-Cl)₂] and [Cu{3,4,5-(CH₃)₃(C₃HN₂)}₄(H₂O)](NO₃)₂, are presented and compared to the 3-methyl-1H-pyrazole and 3,5-di­methyl-1H-pyrozole analogues.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.046
• wR factor = 0.138
• Data-to-parameter ratio = 20.1

Structure: 2

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.135
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0075 Ang.
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N1       - H1       .       0.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16F     ..CL2              2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6E      ..N9               2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B      ..CL1              2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9       ..CL1              2.94 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         40 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT300_ALERT_4_G Atom Site Occupancy of H6A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6C        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6D        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6E        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6F        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7C        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7D        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7E        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7F        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8C        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8D        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8E        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8F        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14F       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15F       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16F       Constrained at        0.5 Check
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C12      - C15      .       1.50 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note

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

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




Datablock: 2


Alert level C
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N1       - H1       .       0.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B     ..O20              2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B     ..N18              2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B     ..O20              2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B     ..N18              2.66 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note

Alert level G
PLAT300_ALERT_4_G Atom Site Occupancy of H6A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6C        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6D        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6E        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6F        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7C        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7D        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7E        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7F        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8C        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8D        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8E        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8F        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14F       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15F       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16F       Constrained at        0.5 Check
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C12      - C15      .       1.50 Ang.
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C13      - C16      .       1.50 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

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

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014) and XPREP (Bruker, 2014); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and X-SEED (Barbour, 2001).

Di-µ-chlorido-bis[chloridobis(3,4,5-trimethyl-1H-pyrazole-\ κN²)copper(II)] (1)

Crystal data

[Cu2Cl4(C6H10N2)4]	Z = 1
Mr = 709.52	F(000) = 366
Triclinic, P1	Dx = 1.484 Mg m^−3
a = 8.887 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.460 (3) Å	Cell parameters from 1932 reflections
c = 11.214 (3) Å	θ = 5.8–55.1°
α = 85.408 (4)°	µ = 1.70 mm^−1
β = 69.978 (4)°	T = 150 K
γ = 64.097 (4)°	Block, green
V = 794.1 (4) Å^3	0.07 × 0.05 × 0.03 mm

Data collection

Bruker SMART APEXII CCD diffractometer	3620 independent reflections
Radiation source: fine focus sealed tube	2472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 27.6°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −11→11
Tmin = 0.660, Tmax = 0.746	k = −12→12
7770 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.094P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.88	(Δ/σ)max < 0.001
3620 reflections	Δρmax = 0.87 e Å^−3
180 parameters	Δρmin = −0.62 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.

Refinement. Reflections omitted from final refinement on account of beamstop truncation: (h k l) 1 1 0; 1 0 0; 0 1 0; 0 0 1; 1 1 1

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	−0.10296 (6)	0.41056 (5)	0.43296 (5)	0.01719 (16)
Cl1	−0.07621 (13)	0.41784 (11)	0.63096 (9)	0.0204 (2)
Cl2	−0.38433 (13)	0.61388 (11)	0.50173 (10)	0.0216 (2)
N9	0.2606 (5)	0.1725 (4)	0.3862 (3)	0.0218 (8)
N2	−0.1329 (4)	0.3931 (4)	0.2643 (3)	0.0197 (7)
N10	0.0972 (4)	0.1950 (4)	0.3908 (3)	0.0201 (7)
N1	−0.2889 (5)	0.3999 (4)	0.2661 (4)	0.0201 (7)
C11	0.1218 (5)	0.0584 (5)	0.3422 (4)	0.0186 (8)
C13	0.3867 (6)	0.0275 (5)	0.3368 (4)	0.0222 (9)
C3	−0.0190 (6)	0.3394 (5)	0.1455 (4)	0.0211 (9)
C5	−0.2781 (6)	0.3542 (5)	0.1527 (4)	0.0224 (9)
C4	−0.1062 (6)	0.3149 (5)	0.0708 (4)	0.0252 (9)
C14	−0.0313 (6)	0.0362 (5)	0.3344 (4)	0.0250 (9)
H14D	0.0120	−0.0703	0.2965	0.037*	0.5
H14F	−0.1182	0.0502	0.4201	0.037*	0.5
H14E	−0.0880	0.1141	0.2814	0.037*	0.5
H14B	−0.1415	0.1330	0.3688	0.037*	0.5
H14A	−0.0113	0.0125	0.2453	0.037*	0.5
H14C	−0.0415	−0.0514	0.3840	0.037*	0.5
C12	0.3018 (6)	−0.0507 (5)	0.3073 (4)	0.0213 (9)
C16	0.5772 (6)	−0.0243 (5)	0.3215 (5)	0.0316 (11)
H16B	0.6475	−0.1334	0.2839	0.047*	0.5
H16A	0.6221	0.0442	0.2656	0.047*	0.5
H16C	0.5873	−0.0176	0.4050	0.047*	0.5
H16D	0.5904	0.0622	0.3525	0.047*	0.5
H16F	0.6158	−0.1154	0.3707	0.047*	0.5
H16E	0.6506	−0.0536	0.2313	0.047*	0.5
C6	0.1712 (6)	0.3110 (6)	0.1056 (4)	0.0282 (10)
H6D	0.2313	0.2721	0.0155	0.042*	0.5
H6F	0.1766	0.4099	0.1180	0.042*	0.5
H6E	0.2305	0.2325	0.1571	0.042*	0.5
H6B	0.1942	0.3375	0.1782	0.042*	0.5
H6A	0.2490	0.1997	0.0757	0.042*	0.5
H6C	0.1951	0.3771	0.0366	0.042*	0.5
C8	−0.4341 (6)	0.3511 (6)	0.1316 (5)	0.0308 (10)
H8B	−0.4000	0.3145	0.0428	0.046*	0.5
H8A	−0.4720	0.2794	0.1881	0.046*	0.5
H8C	−0.5325	0.4575	0.1500	0.046*	0.5
H8D	−0.5363	0.3864	0.2111	0.046*	0.5
H8F	−0.4643	0.4215	0.0658	0.046*	0.5
H8E	−0.4038	0.2434	0.1040	0.046*	0.5
C15	0.3862 (7)	−0.2166 (5)	0.2485 (5)	0.0344 (11)
H15B	0.2947	−0.2410	0.2383	0.052*	0.5
H15A	0.4762	−0.2268	0.1650	0.052*	0.5
H15C	0.4428	−0.2900	0.3038	0.052*	0.5
H15D	0.5144	−0.2642	0.2331	0.052*	0.5
H15F	0.3329	−0.2785	0.3065	0.052*	0.5
H15E	0.3663	−0.2152	0.1676	0.052*	0.5
C7	−0.0263 (7)	0.2544 (6)	−0.0659 (4)	0.0376 (12)
H7B	0.0983	0.2371	−0.0989	0.056*	0.5
H7A	−0.0321	0.1547	−0.0739	0.056*	0.5
H7C	−0.0926	0.3318	−0.1146	0.056*	0.5
H7D	−0.1159	0.2453	−0.0927	0.056*	0.5
H7F	0.0145	0.3277	−0.1177	0.056*	0.5
H7E	0.0750	0.1506	−0.0771	0.056*	0.5
H1	−0.367 (5)	0.427 (4)	0.328 (4)	0.000 (10)*
H9	0.270 (7)	0.251 (7)	0.412 (5)	0.047 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0172 (3)	0.0155 (2)	0.0182 (3)	−0.00545 (19)	−0.0067 (2)	−0.00218 (18)
Cl1	0.0258 (5)	0.0207 (5)	0.0177 (5)	−0.0123 (4)	−0.0084 (4)	0.0022 (4)
Cl2	0.0163 (5)	0.0207 (5)	0.0260 (6)	−0.0066 (4)	−0.0051 (4)	−0.0069 (4)
N9	0.0185 (18)	0.0189 (17)	0.027 (2)	−0.0056 (14)	−0.0095 (16)	−0.0028 (14)
N2	0.0162 (17)	0.0203 (17)	0.0198 (18)	−0.0043 (14)	−0.0074 (15)	−0.0010 (14)
N10	0.0198 (18)	0.0211 (17)	0.0218 (19)	−0.0084 (14)	−0.0102 (15)	−0.0005 (14)
N1	0.0163 (19)	0.0218 (18)	0.0173 (19)	−0.0060 (15)	−0.0027 (16)	−0.0018 (14)
C11	0.024 (2)	0.0166 (18)	0.019 (2)	−0.0097 (16)	−0.0095 (17)	0.0002 (15)
C13	0.021 (2)	0.020 (2)	0.024 (2)	−0.0070 (17)	−0.0067 (18)	0.0004 (17)
C3	0.021 (2)	0.022 (2)	0.018 (2)	−0.0072 (17)	−0.0064 (17)	0.0006 (16)
C5	0.024 (2)	0.020 (2)	0.022 (2)	−0.0045 (17)	−0.0115 (18)	−0.0016 (16)
C4	0.027 (2)	0.026 (2)	0.018 (2)	−0.0064 (18)	−0.0089 (19)	−0.0007 (17)
C14	0.031 (2)	0.021 (2)	0.032 (2)	−0.0140 (19)	−0.018 (2)	0.0071 (18)
C12	0.023 (2)	0.0155 (19)	0.021 (2)	−0.0056 (16)	−0.0060 (18)	−0.0032 (16)
C16	0.021 (2)	0.027 (2)	0.042 (3)	−0.0059 (19)	−0.011 (2)	−0.001 (2)
C6	0.022 (2)	0.035 (2)	0.025 (2)	−0.013 (2)	−0.0042 (19)	0.0009 (19)
C8	0.031 (3)	0.035 (3)	0.033 (3)	−0.014 (2)	−0.018 (2)	0.002 (2)
C15	0.032 (3)	0.026 (2)	0.040 (3)	−0.009 (2)	−0.010 (2)	−0.007 (2)
C7	0.040 (3)	0.046 (3)	0.020 (2)	−0.015 (2)	−0.004 (2)	−0.007 (2)

Geometric parameters (Å, º)

Cu1—N10	1.988 (3)	C16—H16B	0.9800
Cu1—N2	2.026 (3)	C16—H16A	0.9800
Cu1—Cl2	2.2939 (12)	C16—H16C	0.9800
Cu1—Cl1	2.3220 (12)	C16—H16D	0.9800
Cu1—Cl1^i	2.6410 (12)	C16—H16F	0.9800
Cl1—Cu1^i	2.6410 (12)	C16—H16E	0.9800
N9—C13	1.341 (5)	C6—H6D	0.9800
N9—N10	1.356 (5)	C6—H6F	0.9800
N9—H9	0.86 (6)	C6—H6E	0.9800
N2—C3	1.339 (5)	C6—H6B	0.9800
N2—N1	1.353 (5)	C6—H6A	0.9800
N10—C11	1.341 (5)	C6—H6C	0.9800
N1—C5	1.335 (5)	C8—H8B	0.9800
N1—H1	0.75 (4)	C8—H8A	0.9800
C11—C12	1.403 (6)	C8—H8C	0.9800
C11—C14	1.497 (6)	C8—H8D	0.9800
C13—C12	1.388 (6)	C8—H8F	0.9800
C13—C16	1.492 (6)	C8—H8E	0.9800
C3—C4	1.410 (6)	C15—H15B	0.9800
C3—C6	1.495 (6)	C15—H15A	0.9800
C5—C4	1.383 (6)	C15—H15C	0.9800
C5—C8	1.497 (6)	C15—H15D	0.9800
C4—C7	1.490 (6)	C15—H15F	0.9800
C14—H14D	0.9800	C15—H15E	0.9800
C14—H14F	0.9800	C7—H7B	0.9800
C14—H14E	0.9800	C7—H7A	0.9800
C14—H14B	0.9800	C7—H7C	0.9800
C14—H14A	0.9800	C7—H7D	0.9800
C14—H14C	0.9800	C7—H7F	0.9800
C12—C15	1.503 (6)	C7—H7E	0.9800
N10—Cu1—N2	88.98 (14)	C3—C6—H6F	109.5
N10—Cu1—Cl2	161.92 (10)	H6D—C6—H6F	109.5
N2—Cu1—Cl2	88.85 (10)	C3—C6—H6E	109.5
N10—Cu1—Cl1	89.71 (10)	H6D—C6—H6E	109.5
N2—Cu1—Cl1	176.07 (10)	H6F—C6—H6E	109.5
Cl2—Cu1—Cl1	91.26 (4)	C3—C6—H6B	109.5
N10—Cu1—Cl1^i	100.25 (10)	H6D—C6—H6B	141.1
N2—Cu1—Cl1^i	99.04 (10)	H6F—C6—H6B	56.3
Cl2—Cu1—Cl1^i	97.81 (5)	H6E—C6—H6B	56.3
Cl1—Cu1—Cl1^i	84.83 (4)	C3—C6—H6A	109.5
Cu1—Cl1—Cu1^i	95.17 (4)	H6D—C6—H6A	56.3
C13—N9—N10	112.5 (3)	H6F—C6—H6A	141.1
C13—N9—H9	130 (4)	H6E—C6—H6A	56.3
N10—N9—H9	118 (4)	H6B—C6—H6A	109.5
C3—N2—N1	105.8 (3)	C3—C6—H6C	109.5
C3—N2—Cu1	133.9 (3)	H6D—C6—H6C	56.3
N1—N2—Cu1	118.3 (3)	H6F—C6—H6C	56.3
C11—N10—N9	105.3 (3)	H6E—C6—H6C	141.1
C11—N10—Cu1	134.0 (3)	H6B—C6—H6C	109.5
N9—N10—Cu1	119.6 (2)	H6A—C6—H6C	109.5
C5—N1—N2	112.0 (4)	C5—C8—H8B	109.5
C5—N1—H1	129 (3)	C5—C8—H8A	109.5
N2—N1—H1	119 (3)	H8B—C8—H8A	109.5
N10—C11—C12	110.4 (3)	C5—C8—H8C	109.5
N10—C11—C14	121.0 (4)	H8B—C8—H8C	109.5
C12—C11—C14	128.6 (4)	H8A—C8—H8C	109.5
N9—C13—C12	106.5 (4)	C5—C8—H8D	109.5
N9—C13—C16	122.2 (4)	H8B—C8—H8D	141.1
C12—C13—C16	131.4 (4)	H8A—C8—H8D	56.3
N2—C3—C4	109.8 (4)	H8C—C8—H8D	56.3
N2—C3—C6	122.3 (4)	C5—C8—H8F	109.5
C4—C3—C6	127.8 (4)	H8B—C8—H8F	56.3
N1—C5—C4	107.2 (4)	H8A—C8—H8F	141.1
N1—C5—C8	121.7 (4)	H8C—C8—H8F	56.3
C4—C5—C8	131.2 (4)	H8D—C8—H8F	109.5
C5—C4—C3	105.2 (4)	C5—C8—H8E	109.5
C5—C4—C7	128.0 (4)	H8B—C8—H8E	56.3
C3—C4—C7	126.8 (4)	H8A—C8—H8E	56.3
C11—C14—H14D	109.5	H8C—C8—H8E	141.1
C11—C14—H14F	109.5	H8D—C8—H8E	109.5
H14D—C14—H14F	109.5	H8F—C8—H8E	109.5
C11—C14—H14E	109.5	C12—C15—H15B	109.5
H14D—C14—H14E	109.5	C12—C15—H15A	109.5
H14F—C14—H14E	109.5	H15B—C15—H15A	109.5
C11—C14—H14B	109.5	C12—C15—H15C	109.5
H14D—C14—H14B	141.1	H15B—C15—H15C	109.5
H14F—C14—H14B	56.3	H15A—C15—H15C	109.5
H14E—C14—H14B	56.3	C12—C15—H15D	109.5
C11—C14—H14A	109.5	H15B—C15—H15D	141.1
H14D—C14—H14A	56.3	H15A—C15—H15D	56.3
H14F—C14—H14A	141.1	H15C—C15—H15D	56.3
H14E—C14—H14A	56.3	C12—C15—H15F	109.5
H14B—C14—H14A	109.5	H15B—C15—H15F	56.3
C11—C14—H14C	109.5	H15A—C15—H15F	141.1
H14D—C14—H14C	56.3	H15C—C15—H15F	56.3
H14F—C14—H14C	56.3	H15D—C15—H15F	109.5
H14E—C14—H14C	141.1	C12—C15—H15E	109.5
H14B—C14—H14C	109.5	H15B—C15—H15E	56.3
H14A—C14—H14C	109.5	H15A—C15—H15E	56.3
C13—C12—C11	105.5 (3)	H15C—C15—H15E	141.1
C13—C12—C15	127.0 (4)	H15D—C15—H15E	109.5
C11—C12—C15	127.6 (4)	H15F—C15—H15E	109.5
C13—C16—H16B	109.5	C4—C7—H7B	109.5
C13—C16—H16A	109.5	C4—C7—H7A	109.5
H16B—C16—H16A	109.5	H7B—C7—H7A	109.5
C13—C16—H16C	109.5	C4—C7—H7C	109.5
H16B—C16—H16C	109.5	H7B—C7—H7C	109.5
H16A—C16—H16C	109.5	H7A—C7—H7C	109.5
C13—C16—H16D	109.5	C4—C7—H7D	109.5
H16B—C16—H16D	141.1	H7B—C7—H7D	141.1
H16A—C16—H16D	56.3	H7A—C7—H7D	56.3
H16C—C16—H16D	56.3	H7C—C7—H7D	56.3
C13—C16—H16F	109.5	C4—C7—H7F	109.5
H16B—C16—H16F	56.3	H7B—C7—H7F	56.3
H16A—C16—H16F	141.1	H7A—C7—H7F	141.1
H16C—C16—H16F	56.3	H7C—C7—H7F	56.3
H16D—C16—H16F	109.5	H7D—C7—H7F	109.5
C13—C16—H16E	109.5	C4—C7—H7E	109.5
H16B—C16—H16E	56.3	H7B—C7—H7E	56.3
H16A—C16—H16E	56.3	H7A—C7—H7E	56.3
H16C—C16—H16E	141.1	H7C—C7—H7E	141.1
H16D—C16—H16E	109.5	H7D—C7—H7E	109.5
H16F—C16—H16E	109.5	H7F—C7—H7E	109.5
C3—C6—H6D	109.5

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14E···N2	0.98	2.49	3.199 (5)	129
C14—H14E···N1	0.98	2.54	3.401 (6)	147
C14—H14E···N2	0.98	2.49	3.199 (5)	129
C14—H14E···N1	0.98	2.54	3.401 (6)	147
C16—H16F···Cl2^ii	0.98	2.85	3.776 (5)	158
C6—H6E···N9	0.98	2.67	3.521 (6)	146
C6—H6E···N10	0.98	2.55	3.240 (6)	128
C6—H6B···Cl1^i	0.98	2.86	3.692 (5)	144
N1—H1···Cl2	0.75 (4)	2.66 (4)	3.102 (4)	120 (3)
N1—H1···Cl2^iii	0.75 (4)	2.54 (4)	3.214 (4)	151 (3)
N9—H9···Cl1^i	0.86 (6)	2.94 (6)	3.506 (4)	125 (5)
N9—H9···Cl2^i	0.86 (6)	2.37 (6)	3.188 (4)	159 (5)

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

Aquatetrakis(3,4,5-trimethyl-1H-pyrazole-κN²)copper(II) dinitrate (2)

Crystal data

[Cu(C6H10N2)4(H2O)](NO3)2	F(000) = 1364
Mr = 646.21	Dx = 1.354 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.107 (7) Å	Cell parameters from 4118 reflections
b = 7.8939 (16) Å	θ = 5.6–54.8°
c = 20.472 (4) Å	µ = 0.75 mm^−1
β = 102.651 (2)°	T = 150 K
V = 3170.5 (14) Å^3	Plate, blue
Z = 4	0.16 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEXII CCD diffractometer	3636 independent reflections
Radiation source: fine focus sealed tube	2719 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −26→26
Tmin = 0.654, Tmax = 0.746	k = −10→9
13530 measured reflections	l = −26→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
3636 reflections	Δρmax = 0.78 e Å^−3
203 parameters	Δρmin = −0.61 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.

Refinement. Reflections omitted from final refinement on account of beamstop truncation: (h k l) 1 1 0; 2 0 0; 0 1 1; -2 0 2; 0 0 2

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.2500	0.50985 (5)	0.5000	0.01754 (15)
O17	0.2500	0.2345 (3)	0.5000	0.0297 (6)
N2	0.20222 (9)	0.5683 (3)	0.40597 (10)	0.0207 (4)
N9	0.11241 (10)	0.6406 (3)	0.50436 (11)	0.0224 (5)
N10	0.15931 (9)	0.5173 (3)	0.52824 (10)	0.0203 (4)
N1	0.15514 (11)	0.4676 (3)	0.36661 (12)	0.0234 (5)
C5	0.13309 (13)	0.5350 (4)	0.30513 (13)	0.0271 (6)
C11	0.13728 (12)	0.4445 (3)	0.57851 (13)	0.0222 (5)
C12	0.07613 (12)	0.5194 (3)	0.58642 (14)	0.0241 (5)
C15	0.03256 (14)	0.4712 (4)	0.63443 (16)	0.0355 (7)
H15B	0.0540	0.3773	0.6627	0.053*	0.5
H15A	0.0278	0.5688	0.6627	0.053*	0.5
H15C	−0.0126	0.4361	0.6093	0.053*	0.5
H15D	−0.0078	0.5442	0.6271	0.053*	0.5
H15F	0.0184	0.3527	0.6271	0.053*	0.5
H15E	0.0587	0.4854	0.6805	0.053*	0.5
C13	0.06302 (12)	0.6451 (3)	0.53899 (13)	0.0236 (5)
C3	0.21029 (12)	0.7012 (3)	0.36840 (12)	0.0226 (5)
C6	0.25867 (14)	0.8425 (4)	0.39353 (15)	0.0321 (6)
H6D	0.2567	0.9269	0.3580	0.048*	0.5
H6F	0.2460	0.8958	0.4323	0.048*	0.5
H6E	0.3051	0.7975	0.4068	0.048*	0.5
H6B	0.2818	0.8199	0.4400	0.048*	0.5
H6A	0.2925	0.8510	0.3658	0.048*	0.5
H6C	0.2334	0.9493	0.3913	0.048*	0.5
C4	0.16753 (13)	0.6859 (4)	0.30470 (13)	0.0277 (6)
C14	0.17411 (14)	0.3017 (4)	0.61920 (15)	0.0326 (6)
H14D	0.1492	0.2678	0.6532	0.049*	0.5
H14F	0.1771	0.2052	0.5899	0.049*	0.5
H14E	0.2201	0.3387	0.6412	0.049*	0.5
H14B	0.2151	0.2733	0.6029	0.049*	0.5
H14A	0.1872	0.3359	0.6663	0.049*	0.5
H14C	0.1442	0.2025	0.6150	0.049*	0.5
C16	0.00746 (13)	0.7757 (4)	0.52520 (16)	0.0336 (6)
H16B	−0.0235	0.7581	0.5555	0.050*	0.5
H16A	0.0276	0.8891	0.5324	0.050*	0.5
H16C	−0.0180	0.7652	0.4787	0.050*	0.5
H16D	0.0142	0.8501	0.4889	0.050*	0.5
H16F	−0.0369	0.7191	0.5120	0.050*	0.5
H16E	0.0087	0.8430	0.5657	0.050*	0.5
C8	0.08068 (15)	0.4500 (5)	0.25270 (15)	0.0398 (7)
H8B	0.0717	0.5188	0.2119	0.060*	0.5
H8A	0.0973	0.3381	0.2430	0.060*	0.5
H8C	0.0385	0.4369	0.2688	0.060*	0.5
H8D	0.0666	0.3438	0.2705	0.060*	0.5
H8F	0.0410	0.5245	0.2394	0.060*	0.5
H8E	0.0999	0.4257	0.2136	0.060*	0.5
C7	0.15739 (18)	0.8152 (5)	0.24974 (16)	0.0456 (8)
H7B	0.1890	0.9098	0.2633	0.068*	0.5
H7A	0.1662	0.7632	0.2090	0.068*	0.5
H7C	0.1104	0.8572	0.2411	0.068*	0.5
H7D	0.1214	0.7770	0.2123	0.068*	0.5
H7F	0.1442	0.9236	0.2666	0.068*	0.5
H7E	0.2000	0.8296	0.2345	0.068*	0.5
O20	0.10612 (12)	0.1364 (3)	0.37019 (11)	0.0430 (6)
O21	0.07101 (11)	−0.1135 (3)	0.38872 (12)	0.0459 (6)
O19	0.14070 (10)	0.0169 (3)	0.46693 (12)	0.0411 (5)
N18	0.10557 (11)	0.0134 (3)	0.40797 (13)	0.0297 (5)
H1	0.1460 (14)	0.383 (4)	0.3781 (14)	0.021 (8)*
H9	0.1192 (14)	0.702 (4)	0.4685 (15)	0.031 (8)*
H17	0.2176 (14)	0.176 (4)	0.4879 (15)	0.029 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0159 (2)	0.0155 (2)	0.0221 (2)	0.000	0.00595 (15)	0.000
O17	0.0234 (13)	0.0158 (13)	0.0498 (18)	0.000	0.0077 (13)	0.000
N2	0.0208 (10)	0.0173 (10)	0.0246 (11)	−0.0015 (8)	0.0062 (9)	0.0010 (8)
N9	0.0201 (10)	0.0177 (11)	0.0305 (12)	0.0032 (8)	0.0081 (9)	0.0019 (9)
N10	0.0155 (9)	0.0210 (11)	0.0251 (11)	0.0038 (7)	0.0059 (8)	0.0048 (8)
N1	0.0221 (10)	0.0208 (12)	0.0266 (12)	−0.0041 (8)	0.0039 (9)	0.0003 (9)
C5	0.0236 (12)	0.0353 (16)	0.0228 (13)	0.0038 (11)	0.0059 (10)	−0.0024 (11)
C11	0.0203 (11)	0.0198 (12)	0.0275 (13)	−0.0017 (9)	0.0074 (10)	0.0007 (10)
C12	0.0184 (11)	0.0267 (14)	0.0286 (13)	−0.0056 (9)	0.0079 (10)	−0.0052 (10)
C15	0.0283 (13)	0.0450 (19)	0.0368 (16)	−0.0099 (12)	0.0153 (12)	−0.0027 (13)
C13	0.0180 (11)	0.0220 (13)	0.0314 (14)	−0.0015 (9)	0.0068 (10)	−0.0065 (10)
C3	0.0252 (11)	0.0197 (13)	0.0254 (13)	0.0040 (10)	0.0110 (10)	0.0028 (10)
C6	0.0364 (14)	0.0246 (15)	0.0361 (16)	−0.0030 (11)	0.0098 (12)	0.0016 (11)
C4	0.0297 (13)	0.0279 (14)	0.0267 (14)	0.0079 (11)	0.0092 (11)	0.0060 (11)
C14	0.0322 (13)	0.0293 (15)	0.0384 (16)	0.0059 (12)	0.0123 (12)	0.0120 (12)
C16	0.0260 (12)	0.0285 (16)	0.0478 (17)	0.0066 (11)	0.0112 (12)	−0.0046 (13)
C8	0.0327 (15)	0.054 (2)	0.0302 (16)	−0.0032 (14)	0.0023 (13)	−0.0073 (14)
C7	0.0562 (19)	0.046 (2)	0.0343 (17)	0.0078 (16)	0.0099 (15)	0.0147 (15)
O20	0.0552 (13)	0.0259 (11)	0.0454 (13)	−0.0093 (9)	0.0053 (11)	0.0081 (9)
O21	0.0524 (13)	0.0278 (12)	0.0618 (15)	−0.0154 (10)	0.0218 (12)	−0.0101 (10)
O19	0.0271 (10)	0.0432 (13)	0.0493 (13)	−0.0067 (8)	0.0003 (9)	0.0158 (10)
N18	0.0257 (11)	0.0198 (12)	0.0458 (14)	0.0016 (9)	0.0128 (10)	0.0018 (10)

Geometric parameters (Å, º)

Cu1—N2	2.008 (2)	C6—H6B	0.9800
Cu1—N2^i	2.008 (2)	C6—H6A	0.9800
Cu1—N10	2.031 (2)	C6—H6C	0.9800
Cu1—N10^i	2.031 (2)	C4—C7	1.499 (4)
Cu1—O17	2.174 (3)	C14—H14D	0.9800
O17—H17	0.79 (3)	C14—H14F	0.9800
N2—C3	1.332 (3)	C14—H14E	0.9800
N2—N1	1.358 (3)	C14—H14B	0.9800
N9—C13	1.341 (3)	C14—H14A	0.9800
N9—N10	1.369 (3)	C14—H14C	0.9800
N9—H9	0.92 (3)	C16—H16B	0.9800
N10—C11	1.336 (3)	C16—H16A	0.9800
N1—C5	1.349 (4)	C16—H16C	0.9800
N1—H1	0.75 (3)	C16—H16D	0.9800
C5—C4	1.379 (4)	C16—H16F	0.9800
C5—C8	1.489 (4)	C16—H16E	0.9800
C11—C12	1.405 (4)	C8—H8B	0.9800
C11—C14	1.497 (4)	C8—H8A	0.9800
C12—C13	1.373 (4)	C8—H8C	0.9800
C12—C15	1.502 (4)	C8—H8D	0.9800
C15—H15B	0.9800	C8—H8F	0.9800
C15—H15A	0.9800	C8—H8E	0.9800
C15—H15C	0.9800	C7—H7B	0.9800
C15—H15D	0.9800	C7—H7A	0.9800
C15—H15F	0.9800	C7—H7C	0.9800
C15—H15E	0.9800	C7—H7D	0.9800
C13—C16	1.501 (3)	C7—H7F	0.9800
C3—C4	1.401 (4)	C7—H7E	0.9800
C3—C6	1.495 (4)	O20—N18	1.243 (3)
C6—H6D	0.9800	O21—N18	1.234 (3)
C6—H6F	0.9800	O19—N18	1.258 (3)
C6—H6E	0.9800
N2—Cu1—N2^i	153.41 (13)	H14D—C14—H14F	109.5
N2—Cu1—N10	89.73 (8)	C11—C14—H14E	109.5
N2^i—Cu1—N10	89.51 (8)	H14D—C14—H14E	109.5
N2—Cu1—N10^i	89.50 (8)	H14F—C14—H14E	109.5
N2^i—Cu1—N10^i	89.73 (8)	C11—C14—H14B	109.5
N10—Cu1—N10^i	176.69 (12)	H14D—C14—H14B	141.1
N2—Cu1—O17	103.30 (6)	H14F—C14—H14B	56.3
N2^i—Cu1—O17	103.29 (6)	H14E—C14—H14B	56.3
N10—Cu1—O17	91.66 (6)	C11—C14—H14A	109.5
N10^i—Cu1—O17	91.66 (6)	H14D—C14—H14A	56.3
Cu1—O17—H17	126 (2)	H14F—C14—H14A	141.1
C3—N2—N1	106.0 (2)	H14E—C14—H14A	56.3
C3—N2—Cu1	129.93 (17)	H14B—C14—H14A	109.5
N1—N2—Cu1	124.01 (17)	C11—C14—H14C	109.5
C13—N9—N10	111.2 (2)	H14D—C14—H14C	56.3
C13—N9—H9	131.9 (18)	H14F—C14—H14C	56.3
N10—N9—H9	116.9 (18)	H14E—C14—H14C	141.1
C11—N10—N9	105.21 (19)	H14B—C14—H14C	109.5
C11—N10—Cu1	132.58 (16)	H14A—C14—H14C	109.5
N9—N10—Cu1	120.67 (16)	C13—C16—H16B	109.5
C5—N1—N2	111.5 (2)	C13—C16—H16A	109.5
C5—N1—H1	126 (2)	H16B—C16—H16A	109.5
N2—N1—H1	122 (2)	C13—C16—H16C	109.5
N1—C5—C4	106.5 (2)	H16B—C16—H16C	109.5
N1—C5—C8	122.1 (3)	H16A—C16—H16C	109.5
C4—C5—C8	131.4 (3)	C13—C16—H16D	109.5
N10—C11—C12	110.7 (2)	H16B—C16—H16D	141.1
N10—C11—C14	123.0 (2)	H16A—C16—H16D	56.3
C12—C11—C14	126.2 (2)	H16C—C16—H16D	56.3
C13—C12—C11	105.1 (2)	C13—C16—H16F	109.5
C13—C12—C15	126.6 (2)	H16B—C16—H16F	56.3
C11—C12—C15	128.3 (3)	H16A—C16—H16F	141.1
C12—C15—H15B	109.5	H16C—C16—H16F	56.3
C12—C15—H15A	109.5	H16D—C16—H16F	109.5
H15B—C15—H15A	109.5	C13—C16—H16E	109.5
C12—C15—H15C	109.5	H16B—C16—H16E	56.3
H15B—C15—H15C	109.5	H16A—C16—H16E	56.3
H15A—C15—H15C	109.5	H16C—C16—H16E	141.1
C12—C15—H15D	109.5	H16D—C16—H16E	109.5
H15B—C15—H15D	141.1	H16F—C16—H16E	109.5
H15A—C15—H15D	56.3	C5—C8—H8B	109.5
H15C—C15—H15D	56.3	C5—C8—H8A	109.5
C12—C15—H15F	109.5	H8B—C8—H8A	109.5
H15B—C15—H15F	56.3	C5—C8—H8C	109.5
H15A—C15—H15F	141.1	H8B—C8—H8C	109.5
H15C—C15—H15F	56.3	H8A—C8—H8C	109.5
H15D—C15—H15F	109.5	C5—C8—H8D	109.5
C12—C15—H15E	109.5	H8B—C8—H8D	141.1
H15B—C15—H15E	56.3	H8A—C8—H8D	56.3
H15A—C15—H15E	56.3	H8C—C8—H8D	56.3
H15C—C15—H15E	141.1	C5—C8—H8F	109.5
H15D—C15—H15E	109.5	H8B—C8—H8F	56.3
H15F—C15—H15E	109.5	H8A—C8—H8F	141.1
N9—C13—C12	107.7 (2)	H8C—C8—H8F	56.3
N9—C13—C16	121.7 (2)	H8D—C8—H8F	109.5
C12—C13—C16	130.5 (2)	C5—C8—H8E	109.5
N2—C3—C4	110.0 (2)	H8B—C8—H8E	56.3
N2—C3—C6	122.8 (2)	H8A—C8—H8E	56.3
C4—C3—C6	127.2 (2)	H8C—C8—H8E	141.1
C3—C6—H6D	109.5	H8D—C8—H8E	109.5
C3—C6—H6F	109.5	H8F—C8—H8E	109.5
H6D—C6—H6F	109.5	C4—C7—H7B	109.5
C3—C6—H6E	109.5	C4—C7—H7A	109.5
H6D—C6—H6E	109.5	H7B—C7—H7A	109.5
H6F—C6—H6E	109.5	C4—C7—H7C	109.5
C3—C6—H6B	109.5	H7B—C7—H7C	109.5
H6D—C6—H6B	141.1	H7A—C7—H7C	109.5
H6F—C6—H6B	56.3	C4—C7—H7D	109.5
H6E—C6—H6B	56.3	H7B—C7—H7D	141.1
C3—C6—H6A	109.5	H7A—C7—H7D	56.3
H6D—C6—H6A	56.3	H7C—C7—H7D	56.3
H6F—C6—H6A	141.1	C4—C7—H7F	109.5
H6E—C6—H6A	56.3	H7B—C7—H7F	56.3
H6B—C6—H6A	109.5	H7A—C7—H7F	141.1
C3—C6—H6C	109.5	H7C—C7—H7F	56.3
H6D—C6—H6C	56.3	H7D—C7—H7F	109.5
H6F—C6—H6C	56.3	C4—C7—H7E	109.5
H6E—C6—H6C	141.1	H7B—C7—H7E	56.3
H6B—C6—H6C	109.5	H7A—C7—H7E	56.3
H6A—C6—H6C	109.5	H7C—C7—H7E	141.1
C5—C4—C3	106.0 (2)	H7D—C7—H7E	109.5
C5—C4—C7	127.4 (3)	H7F—C7—H7E	109.5
C3—C4—C7	126.5 (3)	O21—N18—O20	121.1 (3)
C11—C14—H14D	109.5	O21—N18—O19	118.8 (2)
C11—C14—H14F	109.5	O20—N18—O19	120.0 (2)

Symmetry code: (i) −x+1/2, y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6E···N9^i	0.98	2.50	3.355 (4)	145
C6—H6E···N10^i	0.98	2.60	3.274 (4)	126
C6—H6F···O19^ii	0.98	2.56	3.367 (4)	140
C6—H6E···N9^i	0.98	2.50	3.355 (4)	145
C6—H6E···N10^i	0.98	2.60	3.274 (4)	126
C14—H14B···O17	0.98	2.38	3.193 (3)	140
C16—H16B···O20^iii	0.98	2.62	3.525 (4)	153
C16—H16B···N18^iii	0.98	2.66	3.342 (4)	127
C16—H16D···O21^ii	0.98	2.57	3.430 (4)	146
C8—H8D···O20	0.98	2.60	3.411 (4)	140
N1—H1···O20	0.75 (3)	2.10 (3)	2.801 (3)	158 (3)
N9—H9···N2	0.92 (3)	2.54 (3)	3.039 (3)	114 (2)
N9—H9···O21^ii	0.92 (3)	2.24 (3)	3.033 (3)	144 (2)
N9—H9···O19^ii	0.92 (3)	2.52 (3)	3.150 (3)	126 (2)
O17—H17···O19	0.79 (3)	1.97 (3)	2.755 (3)	174 (3)
C6—H6F···O19^ii	0.98	2.56	3.367 (4)	140
C6—H6E···N9^i	0.98	2.50	3.355 (4)	145
C6—H6E···N10^i	0.98	2.60	3.274 (4)	126
C6—H6E···N9^i	0.98	2.50	3.355 (4)	145
C6—H6E···N10^i	0.98	2.60	3.274 (4)	126
C14—H14B···O17	0.98	2.38	3.193 (3)	140
C16—H16B···O20^iii	0.98	2.62	3.525 (4)	153
C16—H16B···N18^iii	0.98	2.66	3.342 (4)	127
C16—H16D···O21^ii	0.98	2.57	3.430 (4)	146
C8—H8D···O20	0.98	2.60	3.411 (4)	140
N1—H1···O20	0.75 (3)	2.10 (3)	2.801 (3)	158 (3)
N9—H9···N2	0.92 (3)	2.54 (3)	3.039 (3)	114 (2)
N9—H9···O21^ii	0.92 (3)	2.24 (3)	3.033 (3)	144 (2)
N9—H9···O19^ii	0.92 (3)	2.52 (3)	3.150 (3)	126 (2)
O17—H17···O19	0.79 (3)	1.97 (3)	2.755 (3)	174 (3)

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