Tetra­aqua­bis(3,5-dinitro­benzoato-κO)nickel(II) tetra­hydrate

The Ni atom in the title compound, [Ni(C₇H₃N₂O₆)₂(H₂O)₄]·4H₂O, is covalently bonded to two dinitro­benzoate groups and datively bonded by four water mol­ecules in a trans octa­hedral geometry; adjacent mol­ecules are linked through the uncoord­inated water mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.097
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.519     0.855
            Tmin(prime) and Tmax expected:      0.719     0.851
            RR(prime) =      0.718
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.71
PLAT430_ALERT_2_B Short Inter D...A Contact  O3     ..  O3      ..       2.82 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O9     ..  O9      ..       2.70 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O9     ..  N2      ..       2.80 Ang.
PLAT736_ALERT_1_B H...A   Calc     1.95(2), Rep     1.95(9) ......       4.50 su-Ra
              H3#  -O5W     1.555   2.566

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     -   N2      ..       5.85 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1W     ..       5.40 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.01
PLAT432_ALERT_2_C Short Inter X...Y Contact  O9     ..  C6      ..       3.01 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         16
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O8W  -H8W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O8W  -H8W2    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O8W  -H15#    1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.95(3), Rep   1.960(10) ......       3.00 su-Ra
              H15# -O8      1.555   2.656

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: atomic coordinates taken from the isostructural Co analog (Tahir et al., 1996)'; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Tetraaquabis(3,5-dinitrobenzoate-κO)nickel(II) tetrahydrate

Crystal data

[Ni(C7H3N2O6)2(H2O)4]·4H2O	Z = 2
Mr = 625.07	F(000) = 644
Triclinic, P1	Dx = 1.706 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1835 (2) Å	Cell parameters from 10360 reflections
b = 11.7581 (3) Å	θ = 3.0–27.5°
c = 15.0077 (4) Å	µ = 0.90 mm^−1
α = 103.199 (1)°	T = 295 K
β = 98.267 (1)°	Prism, green
γ = 92.672 (1)°	0.36 × 0.25 × 0.18 mm
V = 1217.15 (6) Å^3

Data collection

Rigaku R-AXIS RAPID IP diffractometer	5527 independent reflections
Radiation source: fine-focus sealed tube	4813 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.519, Tmax = 0.855	k = −15→13
12071 measured reflections	l = −19→19

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 0.1168P] where P = (Fo^2 + 2Fc^2)/3
5527 reflections	(Δ/σ)max = 0.001
416 parameters	Δρmax = 0.36 e Å^−3
24 restraints	Δρmin = −0.67 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ni1	0.23406 (3)	0.24790 (1)	0.49576 (1)	0.02768 (8)
O1	0.1338 (2)	0.2268 (1)	0.6106 (1)	0.0360 (3)
O2	0.0842 (2)	0.4083 (1)	0.6840 (1)	0.0489 (3)
O3	−0.1820 (2)	0.4410 (1)	0.9770 (1)	0.0496 (3)
O4	−0.0643 (3)	0.3306 (2)	1.0634 (1)	0.0745 (5)
O5	0.0011 (2)	−0.0731 (1)	0.8878 (1)	0.0605 (4)
O6	0.1363 (3)	−0.0862 (1)	0.7665 (1)	0.0610 (4)
O7	0.3405 (2)	0.2714 (1)	0.3834 (1)	0.0388 (3)
O8	0.3174 (2)	0.0910 (1)	0.2911 (1)	0.0503 (4)
O9	0.3708 (2)	0.0625 (1)	−0.0375 (1)	0.0506 (3)
O10	0.5468 (3)	0.1964 (2)	−0.0687 (1)	0.0695 (5)
O11	0.5738 (2)	0.5891 (1)	0.1353 (1)	0.0585 (4)
O12	0.4297 (3)	0.6094 (1)	0.2540 (1)	0.0615 (4)
O1w	0.3133 (2)	0.4229 (1)	0.5546 (1)	0.0376 (3)
O2w	−0.0318 (2)	0.2807 (1)	0.4361 (1)	0.0439 (3)
O3w	0.1527 (2)	0.0728 (1)	0.4380 (1)	0.0382 (3)
O4w	0.4999 (2)	0.2106 (1)	0.5535 (1)	0.0395 (3)
O5w	0.2489 (2)	0.5821 (1)	0.4470 (1)	0.0437 (3)
O6w	−0.0742 (3)	0.3489 (2)	0.2736 (1)	0.0780 (6)
O7w	0.2781 (2)	−0.0704 (1)	0.5567 (1)	0.0429 (3)
O8w	0.5127 (3)	0.1119 (2)	0.7093 (1)	0.0627 (4)
N1	−0.1012 (2)	0.3558 (1)	0.9887 (1)	0.0434 (3)
N2	0.0578 (2)	−0.0321 (1)	0.8276 (1)	0.0437 (4)
N3	0.4578 (2)	0.1589 (1)	−0.0168 (1)	0.0395 (3)
N4	0.4913 (2)	0.5498 (1)	0.1889 (1)	0.0403 (3)
C1	0.0908 (2)	0.3008 (1)	0.6778 (1)	0.0310 (3)
C2	0.0446 (2)	0.2524 (1)	0.7577 (1)	0.0282 (3)
C3	−0.0111 (2)	0.3250 (1)	0.8343 (1)	0.0311 (3)
C4	−0.0433 (2)	0.2773 (1)	0.9075 (1)	0.0334 (3)
C5	−0.0227 (2)	0.1617 (2)	0.9084 (1)	0.0354 (3)
C6	0.0304 (2)	0.0927 (1)	0.8307 (1)	0.0317 (3)
C7	0.0643 (2)	0.1345 (1)	0.7551 (1)	0.0297 (3)
C8	0.3498 (2)	0.1999 (1)	0.3083 (1)	0.0336 (3)
C9	0.3979 (2)	0.2531 (1)	0.2310 (1)	0.0312 (3)
C10	0.4108 (2)	0.1817 (1)	0.1446 (1)	0.0329 (3)
C11	0.4511 (2)	0.2342 (1)	0.0752 (1)	0.0327 (3)
C12	0.4806 (2)	0.3538 (2)	0.0871 (1)	0.0341 (3)
C13	0.4638 (2)	0.4212 (1)	0.1731 (1)	0.0324 (3)
C14	0.4230 (2)	0.3747 (1)	0.2454 (1)	0.0316 (3)
H3	−0.0265	0.4036	0.8364	0.037*
H5	−0.0435	0.1319	0.9588	0.042*
H7	0.0995	0.0850	0.7036	0.036*
H10	0.3928	0.1006	0.1337	0.040*
H12	0.5102	0.3870	0.0398	0.041*
H14	0.4125	0.4234	0.3025	0.038*
H1w1	0.249 (3)	0.440 (2)	0.598 (1)	0.07 (1)*
H1w2	0.299 (3)	0.471 (2)	0.520 (1)	0.06 (1)*
H2w1	−0.102 (3)	0.321 (2)	0.470 (1)	0.07 (1)*
H2w2	−0.031 (4)	0.306 (2)	0.387 (1)	0.08 (1)*
H3w1	0.208 (3)	0.061 (2)	0.391 (1)	0.06 (1)*
H3w2	0.185 (3)	0.026 (2)	0.471 (1)	0.06 (1)*
H4w1	0.567 (3)	0.170 (2)	0.518 (1)	0.06 (1)*
H4w2	0.502 (4)	0.183 (2)	0.602 (1)	0.08 (1)*
H5w1	0.173 (3)	0.563 (2)	0.397 (1)	0.08 (1)*
H5w2	0.342 (2)	0.624 (2)	0.441 (2)	0.07 (1)*
H6w1	−0.063 (4)	0.417 (1)	0.266 (2)	0.08 (1)*
H6w2	−0.066 (5)	0.298 (2)	0.226 (1)	0.10 (1)*
H7w1	0.336 (3)	−0.028 (2)	0.607 (1)	0.06 (1)*
H7w2	0.187 (2)	−0.112 (2)	0.566 (2)	0.07 (1)*
H8w1	0.567 (4)	0.058 (2)	0.730 (2)	0.08 (1)*
H8w2	0.501 (5)	0.169 (2)	0.754 (2)	0.13 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0392 (1)	0.0265 (1)	0.0206 (1)	0.0040 (1)	0.0113 (1)	0.0078 (1)
O1	0.0578 (7)	0.0307 (5)	0.0248 (5)	0.0058 (5)	0.0193 (5)	0.0090 (5)
O2	0.090 (1)	0.0301 (6)	0.0352 (6)	0.0131 (6)	0.0268 (7)	0.0137 (5)
O3	0.0532 (8)	0.0479 (7)	0.0476 (7)	0.0084 (6)	0.0241 (6)	0.0003 (6)
O4	0.121 (2)	0.0817 (11)	0.0264 (7)	0.020 (1)	0.0269 (8)	0.0130 (7)
O5	0.088 (1)	0.0475 (8)	0.0504 (8)	−0.0134 (7)	0.0034 (7)	0.0296 (7)
O6	0.100 (1)	0.0323 (7)	0.0532 (9)	0.0156 (7)	0.0178 (8)	0.0089 (6)
O7	0.0601 (8)	0.0349 (6)	0.0251 (5)	0.0014 (5)	0.0185 (5)	0.0083 (5)
O8	0.090 (1)	0.0327 (6)	0.0345 (6)	0.0059 (6)	0.0258 (7)	0.0098 (5)
O9	0.0647 (9)	0.0462 (7)	0.0343 (6)	0.0045 (6)	0.0022 (6)	−0.0005 (6)
O10	0.099 (1)	0.078 (1)	0.0334 (7)	−0.0066 (9)	0.0357 (8)	0.0041 (7)
O11	0.071 (1)	0.0517 (8)	0.0586 (9)	−0.0129 (7)	0.0109 (7)	0.0275 (7)
O12	0.099 (1)	0.0350 (7)	0.0513 (8)	0.0091 (7)	0.0190 (8)	0.0057 (6)
O1w	0.0565 (7)	0.0291 (6)	0.0301 (6)	0.0033 (5)	0.0129 (5)	0.0092 (5)
O2w	0.0486 (7)	0.0533 (8)	0.0363 (7)	0.0174 (6)	0.0123 (5)	0.0179 (6)
O3w	0.0553 (7)	0.0305 (6)	0.0302 (6)	0.0008 (5)	0.0130 (5)	0.0068 (5)
O4w	0.0431 (7)	0.0438 (7)	0.0360 (6)	0.0123 (5)	0.0115 (5)	0.0131 (6)
O5w	0.0454 (7)	0.0441 (7)	0.0471 (8)	0.0052 (6)	0.0119 (6)	0.0191 (6)
O6w	0.146 (2)	0.0491 (9)	0.0406 (8)	0.026 (1)	0.010 (1)	0.0135 (8)
O7w	0.0458 (7)	0.0412 (7)	0.0433 (7)	0.0024 (5)	0.0146 (6)	0.0091 (6)
O8w	0.081 (1)	0.067 (1)	0.0463 (8)	0.0298 (9)	0.0138 (8)	0.0179 (8)
N1	0.0530 (9)	0.0505 (8)	0.0278 (7)	0.0001 (7)	0.0187 (6)	0.0050 (6)
N2	0.060 (1)	0.0313 (7)	0.0394 (8)	−0.0041 (6)	−0.0008 (7)	0.0153 (7)
N3	0.0463 (8)	0.0490 (8)	0.0232 (6)	0.0101 (7)	0.0081 (6)	0.0057 (6)
N4	0.0505 (9)	0.0344 (7)	0.0352 (7)	−0.0010 (6)	0.0001 (6)	0.0118 (6)
C1	0.0423 (8)	0.0314 (7)	0.0229 (7)	0.0061 (6)	0.0102 (6)	0.0101 (6)
C2	0.0351 (8)	0.0303 (7)	0.0217 (6)	0.0038 (6)	0.0086 (5)	0.0087 (6)
C3	0.0379 (8)	0.0306 (7)	0.0271 (7)	0.0057 (6)	0.0110 (6)	0.0076 (6)
C4	0.0376 (8)	0.0397 (8)	0.0240 (7)	0.0027 (6)	0.0116 (6)	0.0060 (6)
C5	0.0432 (9)	0.0417 (9)	0.0246 (7)	−0.0014 (7)	0.0078 (6)	0.0142 (7)
C6	0.0382 (8)	0.0298 (7)	0.0284 (7)	−0.0005 (6)	0.0046 (6)	0.0108 (6)
C7	0.0377 (8)	0.0293 (7)	0.0226 (7)	0.0017 (6)	0.0073 (6)	0.0061 (6)
C8	0.0444 (9)	0.0342 (8)	0.0260 (7)	0.0068 (6)	0.0127 (6)	0.0102 (7)
C9	0.0381 (8)	0.0346 (8)	0.0238 (7)	0.0050 (6)	0.0104 (6)	0.0088 (6)
C10	0.0406 (8)	0.0332 (8)	0.0264 (7)	0.0048 (6)	0.0106 (6)	0.0064 (6)
C11	0.0357 (8)	0.0408 (8)	0.0226 (7)	0.0059 (6)	0.0085 (6)	0.0066 (6)
C12	0.0374 (8)	0.0430 (9)	0.0255 (7)	0.0019 (6)	0.0092 (6)	0.0133 (7)
C13	0.0357 (8)	0.0329 (8)	0.0308 (8)	0.0017 (6)	0.0064 (6)	0.0113 (7)
C14	0.0385 (8)	0.0336 (8)	0.0236 (7)	0.0043 (6)	0.0084 (6)	0.0060 (6)

Geometric parameters (Å, º)

Ni1—O1	2.022 (1)	C8—C9	1.511 (2)
Ni1—O7	2.017 (1)	C9—C10	1.393 (2)
Ni1—O1w	2.063 (1)	C9—C14	1.395 (2)
Ni1—O2w	2.081 (1)	C10—C11	1.383 (2)
Ni1—O3w	2.064 (1)	C11—C12	1.378 (2)
Ni1—O4w	2.090 (1)	C12—C13	1.377 (2)
O1—C1	1.257 (2)	C13—C14	1.382 (2)
O2—C1	1.250 (2)	O1w—H1w1	0.85 (1)
O3—N1	1.216 (2)	O1w—H1w2	0.85 (1)
O4—N1	1.220 (2)	O2w—H2w1	0.85 (1)
O5—N2	1.225 (2)	O2w—H2w2	0.85 (1)
O6—N2	1.217 (2)	O3w—H3w1	0.85 (1)
O7—C8	1.255 (2)	O3w—H3w2	0.85 (1)
O8—C8	1.251 (2)	O4w—H4w1	0.85 (1)
O9—N3	1.220 (2)	O4w—H4w2	0.85 (1)
O10—N3	1.218 (2)	O5w—H5w1	0.84 (1)
O11—N4	1.223 (2)	O5w—H5w2	0.84 (1)
O12—N4	1.217 (2)	O6w—H6w1	0.84 (1)
N1—C4	1.475 (2)	O6w—H6w2	0.84 (1)
N2—C6	1.481 (2)	O7w—H7w1	0.84 (1)
N3—C11	1.470 (2)	O7w—H7w2	0.84 (1)
N4—C13	1.474 (2)	O8w—H8w1	0.85 (1)
C1—C2	1.510 (2)	O8w—H8w2	0.85 (1)
C2—C3	1.388 (2)	C3—H3	0.93
C2—C7	1.391 (2)	C5—H5	0.93
C3—C4	1.385 (2)	C7—H7	0.93
C4—C5	1.378 (2)	C10—H10	0.93
C5—C6	1.375 (2)	C12—H12	0.93
C6—C7	1.382 (2)	C14—H14	0.93
O1—Ni1—O7	178.43 (5)	O8—C8—O7	126.5 (1)
O1—Ni1—O1w	91.82 (5)	O8—C8—C9	117.9 (1)
O1—Ni1—O2w	91.28 (5)	O7—C8—C9	115.6 (1)
O1—Ni1—O3w	87.58 (5)	C10—C9—C14	119.9 (1)
O1—Ni1—O4w	89.01 (5)	C10—C9—C8	120.4 (1)
O7—Ni1—O1w	87.07 (5)	C14—C9—C8	119.7 (1)
O7—Ni1—O2w	89.89 (5)	C11—C10—C9	118.5 (1)
O7—Ni1—O3w	93.54 (5)	C12—C11—C10	123.5 (1)
O7—Ni1—O4w	89.84 (5)	C12—C11—N3	118.2 (1)
O1w—Ni1—O2w	93.38 (5)	C10—C11—N3	118.3 (1)
O1w—Ni1—O3w	179.36 (4)	C13—C12—C11	116.2 (1)
O1w—Ni1—O4w	88.07 (5)	C12—C13—C14	123.4 (2)
O2w—Ni1—O3w	86.40 (5)	C12—C13—N4	118.3 (1)
O2w—Ni1—O4w	178.51 (4)	C14—C13—N4	118.4 (1)
O3w—Ni1—O4w	92.15 (5)	C13—C14—C9	118.6 (1)
C1—O1—Ni1	130.9 (1)	Ni1—O1w—H1w1	104 (2)
C8—O7—Ni1	130.2 (1)	Ni1—O1w—H1w2	118 (2)
O3—N1—O4	124.3 (2)	H1w1—O1w—H1w2	110 (1)
O3—N1—C4	118.2 (1)	Ni1—O2w—H2w1	119 (2)
O4—N1—C4	117.5 (2)	Ni1—O2w—H2w2	114 (2)
O6—N2—O5	124.7 (2)	H2w1—O2w—H2w2	109 (1)
O6—N2—C6	118.0 (1)	Ni1—O3w—H3w1	101 (2)
O5—N2—C6	117.3 (2)	Ni1—O3w—H3w2	116 (2)
O10—N3—O9	123.6 (2)	H3w1—O3w—H3w2	110 (1)
O10—N3—C11	118.5 (2)	Ni1—O4w—H4w1	118 (2)
O9—N3—C11	117.8 (1)	Ni1—O4w—H4w2	115 (2)
O12—N4—O11	124.5 (2)	H4w1—O4w—H4w2	108 (1)
O12—N4—C13	117.9 (1)	H5w1—O5w—H5w2	110 (2)
O11—N4—C13	117.6 (2)	H6w1—O6w—H6w2	112 (2)
O2—C1—O1	126.3 (1)	H7w1—O7w—H7w2	111 (2)
O2—C1—C2	118.3 (1)	H8w1—O8w—H8w2	110 (2)
O1—C1—C2	115.4 (1)	C4—C3—H3	120.9
C3—C2—C7	120.2 (1)	C2—C3—H3	120.9
C3—C2—C1	120.6 (1)	C6—C5—H5	121.9
C7—C2—C1	119.2 (1)	C4—C5—H5	121.9
C4—C3—C2	118.3 (1)	C6—C7—H7	120.7
C5—C4—C3	123.4 (1)	C2—C7—H7	120.7
C5—C4—N1	118.9 (1)	C11—C10—H10	120.8
C3—C4—N1	117.6 (1)	C9—C10—H10	120.8
C6—C5—C4	116.3 (1)	C13—C12—H12	121.9
C5—C6—C7	123.2 (2)	C11—C12—H12	121.9
C5—C6—N2	119.0 (1)	C13—C14—H14	120.7
C7—C6—N2	117.7 (2)	C9—C14—H14	120.7
C6—C7—C2	118.6 (1)
O1w—Ni1—O1—C1	17.2 (2)	C5—C6—C7—C2	0.3 (2)
O3w—Ni1—O1—C1	−162.6 (2)	N2—C6—C7—C2	−178.2 (1)
O2w—Ni1—O1—C1	−76.2 (2)	C3—C2—C7—C6	−1.1 (2)
O4w—Ni1—O1—C1	105.2 (2)	C1—C2—C7—C6	176.9 (1)
O1w—Ni1—O7—C8	179.6 (2)	Ni1—O7—C8—O8	−11.0 (3)
O3w—Ni1—O7—C8	−0.6 (2)	Ni1—O7—C8—C9	166.6 (1)
O2w—Ni1—O7—C8	−87.0 (2)	O8—C8—C9—C10	−1.9 (2)
O4w—Ni1—O7—C8	91.5 (2)	O7—C8—C9—C10	−179.6 (2)
Ni1—O1—C1—O2	7.4 (3)	O8—C8—C9—C14	175.9 (2)
Ni1—O1—C1—C2	−172.1 (1)	O7—C8—C9—C14	−1.9 (2)
O2—C1—C2—C3	2.6 (2)	C14—C9—C10—C11	0.8 (2)
O1—C1—C2—C3	−177.8 (1)	C8—C9—C10—C11	178.6 (1)
O2—C1—C2—C7	−175.4 (2)	C9—C10—C11—C12	0.5 (2)
O1—C1—C2—C7	4.2 (2)	C9—C10—C11—N3	−177.8 (1)
C7—C2—C3—C4	0.9 (2)	O10—N3—C11—C12	23.9 (2)
C1—C2—C3—C4	−177.1 (1)	O9—N3—C11—C12	−154.9 (2)
C2—C3—C4—C5	0.1 (2)	O10—N3—C11—C10	−157.7 (2)
C2—C3—C4—N1	179.6 (1)	O9—N3—C11—C10	23.6 (2)
O3—N1—C4—C5	−154.4 (2)	C10—C11—C12—C13	−1.4 (2)
O4—N1—C4—C5	25.7 (2)	N3—C11—C12—C13	176.9 (1)
O3—N1—C4—C3	26.0 (2)	C11—C12—C13—C14	1.1 (2)
O4—N1—C4—C3	−153.9 (2)	C11—C12—C13—N4	−179.1 (1)
C3—C4—C5—C6	−0.9 (2)	O12—N4—C13—C12	161.2 (2)
N1—C4—C5—C6	179.6 (2)	O11—N4—C13—C12	−18.5 (2)
C4—C5—C6—C7	0.7 (2)	O12—N4—C13—C14	−19.0 (2)
C4—C5—C6—N2	179.1 (2)	O11—N4—C13—C14	161.3 (2)
O6—N2—C6—C5	−167.2 (2)	C12—C13—C14—C9	0.2 (3)
O5—N2—C6—C5	12.2 (2)	N4—C13—C14—C9	−179.6 (2)
O6—N2—C6—C7	11.3 (2)	C10—C9—C14—C13	−1.2 (2)
O5—N2—C6—C7	−169.3 (2)	C8—C9—C14—C13	−178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O2	0.85 (1)	1.96 (1)	2.749 (2)	156 (2)
O1w—H1w2···O5w	0.85 (1)	1.91 (1)	2.752 (2)	175 (2)
O2w—H2w1···O5w^i	0.85 (1)	1.95 (9)	2.801 (2)	177 (3)
O2w—H2w2···O6w	0.85 (1)	1.88 (1)	2.718 (2)	170 (3)
O3w—H3w1···O8	0.85 (1)	1.88 (1)	2.692 (2)	159 (2)
O3w—H3w2···O7w	0.85 (1)	1.96 (1)	2.806 (2)	174 (2)
O4w—H4w1···O7w^ii	0.85 (1)	1.93 (1)	2.784 (2)	175 (2)
O4w—H4w2···O8w	0.85 (1)	1.98 (1)	2.830 (2)	177 (2)
O5w—H5w1···O2^i	0.84 (1)	2.14 (2)	2.894 (2)	148 (3)
O5w—H5w2···O4w^iii	0.84 (1)	2.18 (1)	2.967 (2)	155 (2)
O6w—H6w1···O2^i	0.84 (1)	2.04 (2)	2.786 (2)	148 (2)
O7w—H7w2···O2w^iv	0.84 (1)	2.23 (1)	3.004 (2)	154 (2)
O7w—H7w1···O8w	0.84 (1)	2.18 (1)	2.999 (2)	163 (2)
O8w—H8w1···O8^ii	0.85 (1)	1.96 (1)	2.729 (2)	151 (2)

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