Poly[aqua-μ₃-p-amino­benzoato-κ³N:O:O′-μ₂-p-amino­benzoato-κ²O:O′-p-amino­benzoato-κ²O,O′-gadolinium(III)]

In the title compound, [Gd(C₇H₆NO₂)₃(H₂O)]_n, a two-dimensional coordination polymer, the eight-coordinate Gd^III ions are bridged by two carboxyl­ate groups from two μ₂-p-amino­benzoate ligands, forming a centrosymmetric dinuclear block. These blocks are further connected by μ₃-p-amino­benzoate ligands, yielding a two-dimensional network. The coordination polymers thus formed are connected via hydrogen bonds, producing a three-dimensional supra­molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.054
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2B    ...          ?

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Poly[aqua-µ₃-p-aminobenzoato-κ³N:O:O'-µ₂-p- aminobenzoato-κ²O:O'-p-aminobenzoato-κ²O,O'-gadolinium(III)]

Crystal data

[Gd(C7H6NO2)3(H2O)]	F(000) = 1148
Mr = 583.65	Dx = 1.792 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1516 reflections
a = 9.7639 (18) Å	θ = 2.8–28.1°
b = 22.836 (4) Å	µ = 3.11 mm^−1
c = 9.8496 (18) Å	T = 291 K
β = 99.908 (4)°	Block, red
V = 2163.4 (7) Å^3	0.46 × 0.33 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	3994 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
Tmin = 0.310, Tmax = 0.534	k = −29→29
13405 measured reflections	l = −12→11

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0217P)^2 + 1.9268P] where P = (Fo^2 + 2Fc^2)/3
4828 reflections	(Δ/σ)max = 0.006
307 parameters	Δρmax = 0.47 e Å^−3
9 restraints	Δρmin = −1.17 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Gd1	0.481002 (12)	0.998608 (5)	0.256346 (11)	0.01769 (5)
O1	0.51125 (19)	0.89287 (8)	0.2165 (2)	0.0275 (4)
O2	0.6586 (2)	0.93347 (8)	0.38588 (19)	0.0268 (4)
O3	0.3678 (2)	0.95939 (8)	0.4225 (2)	0.0298 (4)
O4	0.3961 (2)	0.92180 (9)	0.6321 (2)	0.0342 (5)
O5	0.30116 (18)	0.97271 (8)	0.07559 (18)	0.0243 (4)
O6	0.3451 (2)	1.01134 (8)	−0.1192 (2)	0.0265 (4)
O7	0.4568 (2)	1.08569 (8)	0.09586 (19)	0.0264 (4)
H1W	0.427 (3)	1.0730 (12)	0.0150 (15)	0.032*
H2W	0.526 (2)	1.1082 (11)	0.098 (3)	0.032*
N1	0.8296 (3)	0.66183 (11)	0.4750 (3)	0.0357 (6)
H1A	0.889 (3)	0.6614 (13)	0.550 (2)	0.043*
H1B	0.765 (2)	0.6364 (11)	0.470 (3)	0.043*
N2	0.1106 (4)	0.70572 (13)	0.2757 (4)	0.0552 (9)
H2A	0.082 (4)	0.6819 (14)	0.331 (3)	0.066*
H2B	0.066 (4)	0.7080 (16)	0.1934 (17)	0.066*
N3	−0.2859 (2)	0.92780 (9)	−0.3130 (2)	0.0236 (5)
H3A	−0.3082	0.8916	−0.2879	0.028*
H3B	−0.2905	0.9273	−0.4051	0.028*
C1	0.6106 (3)	0.88810 (11)	0.3180 (3)	0.0238 (6)
C2	0.6691 (3)	0.82924 (11)	0.3590 (3)	0.0250 (6)
C3	0.5905 (3)	0.77907 (12)	0.3199 (3)	0.0322 (7)
H3	0.5020	0.7827	0.2676	0.039*
C4	0.6429 (3)	0.72379 (12)	0.3585 (3)	0.0354 (7)
H4	0.5896	0.6907	0.3316	0.042*
C5	0.7751 (3)	0.71787 (12)	0.4373 (3)	0.0299 (6)
C6	0.8532 (3)	0.76797 (12)	0.4772 (3)	0.0332 (7)
H6	0.9414	0.7644	0.5302	0.040*
C7	0.8007 (3)	0.82308 (12)	0.4386 (3)	0.0313 (7)
H7	0.8538	0.8562	0.4661	0.038*
C8	0.3520 (3)	0.91848 (11)	0.5039 (3)	0.0225 (5)
C9	0.2802 (3)	0.86365 (11)	0.4481 (3)	0.0242 (6)
C10	0.2780 (3)	0.81387 (12)	0.5298 (3)	0.0325 (7)
H10	0.3147	0.8157	0.6233	0.039*
C11	0.2220 (3)	0.76187 (13)	0.4735 (3)	0.0397 (8)
H11	0.2235	0.7289	0.5291	0.048*
C12	0.1639 (3)	0.75835 (13)	0.3355 (3)	0.0372 (7)
C13	0.1604 (3)	0.80859 (13)	0.2537 (3)	0.0368 (7)
H13	0.1177	0.8073	0.1618	0.044*
C14	0.2200 (3)	0.86010 (12)	0.3091 (3)	0.0318 (7)
H14	0.2201	0.8928	0.2529	0.038*
C15	0.2661 (3)	0.98444 (10)	−0.0507 (3)	0.0196 (5)
C16	0.1243 (3)	0.96686 (10)	−0.1223 (3)	0.0202 (5)
C17	0.0378 (3)	0.93360 (11)	−0.0541 (3)	0.0239 (6)
H17	0.0695	0.9213	0.0358	0.029*
C18	−0.0949 (3)	0.91866 (11)	−0.1187 (3)	0.0245 (6)
H18	−0.1507	0.8953	−0.0732	0.029*
C19	−0.1451 (3)	0.93860 (11)	−0.2519 (3)	0.0220 (5)
C20	−0.0589 (3)	0.97182 (14)	−0.3202 (3)	0.0305 (7)
H20	−0.0915	0.9850	−0.4093	0.037*
C21	0.0749 (3)	0.98545 (12)	−0.2568 (3)	0.0287 (6)
H21	0.1324	1.0071	−0.3040	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Gd1	0.01726 (7)	0.01899 (7)	0.01579 (7)	−0.00164 (5)	−0.00006 (4)	0.00038 (5)
O1	0.0301 (10)	0.0223 (9)	0.0260 (10)	0.0002 (8)	−0.0067 (8)	0.0000 (8)
O2	0.0312 (11)	0.0224 (9)	0.0234 (10)	0.0011 (8)	−0.0045 (8)	−0.0014 (7)
O3	0.0360 (12)	0.0230 (9)	0.0329 (11)	−0.0074 (8)	0.0131 (9)	0.0019 (8)
O4	0.0386 (12)	0.0348 (11)	0.0260 (11)	−0.0109 (9)	−0.0035 (9)	−0.0030 (9)
O5	0.0219 (10)	0.0278 (9)	0.0201 (10)	−0.0034 (8)	−0.0045 (7)	0.0032 (7)
O6	0.0203 (10)	0.0351 (10)	0.0242 (10)	−0.0041 (8)	0.0040 (8)	0.0013 (8)
O7	0.0312 (11)	0.0266 (10)	0.0210 (10)	−0.0063 (8)	0.0033 (8)	−0.0004 (8)
N1	0.0395 (16)	0.0256 (12)	0.0414 (16)	0.0105 (11)	0.0053 (12)	0.0048 (11)
N2	0.067 (2)	0.0373 (16)	0.063 (2)	−0.0239 (15)	0.0153 (18)	−0.0160 (15)
N3	0.0199 (11)	0.0291 (11)	0.0202 (12)	−0.0034 (9)	−0.0005 (9)	0.0005 (9)
C1	0.0257 (14)	0.0239 (13)	0.0210 (14)	0.0025 (11)	0.0018 (11)	0.0026 (10)
C2	0.0298 (15)	0.0215 (12)	0.0229 (14)	0.0032 (11)	0.0022 (11)	0.0032 (10)
C3	0.0317 (16)	0.0257 (14)	0.0356 (17)	0.0022 (12)	−0.0042 (13)	0.0021 (12)
C4	0.0394 (18)	0.0226 (13)	0.0411 (18)	−0.0006 (12)	−0.0017 (14)	0.0005 (12)
C5	0.0352 (16)	0.0269 (14)	0.0291 (16)	0.0105 (12)	0.0099 (12)	0.0049 (11)
C6	0.0268 (15)	0.0331 (15)	0.0380 (17)	0.0070 (12)	0.0011 (13)	0.0025 (13)
C7	0.0297 (16)	0.0250 (13)	0.0369 (17)	0.0001 (11)	−0.0004 (13)	0.0010 (12)
C8	0.0179 (13)	0.0236 (12)	0.0262 (15)	−0.0024 (10)	0.0044 (10)	−0.0027 (11)
C9	0.0230 (14)	0.0252 (13)	0.0243 (14)	−0.0060 (10)	0.0040 (11)	0.0006 (11)
C10	0.0337 (16)	0.0333 (15)	0.0288 (16)	−0.0071 (12)	0.0003 (13)	0.0022 (12)
C11	0.0446 (19)	0.0262 (14)	0.049 (2)	−0.0068 (13)	0.0101 (15)	0.0092 (14)
C12	0.0347 (17)	0.0305 (15)	0.049 (2)	−0.0134 (13)	0.0140 (14)	−0.0099 (14)
C13	0.0411 (18)	0.0421 (17)	0.0259 (16)	−0.0146 (14)	0.0020 (13)	−0.0065 (13)
C14	0.0392 (17)	0.0299 (14)	0.0247 (15)	−0.0107 (12)	0.0006 (12)	0.0030 (11)
C15	0.0184 (13)	0.0201 (11)	0.0200 (13)	0.0024 (9)	0.0022 (10)	−0.0034 (9)
C16	0.0168 (12)	0.0224 (12)	0.0204 (13)	0.0000 (10)	0.0004 (10)	−0.0018 (10)
C17	0.0228 (13)	0.0281 (13)	0.0181 (13)	0.0005 (11)	−0.0037 (11)	0.0042 (10)
C18	0.0225 (14)	0.0269 (13)	0.0229 (14)	−0.0039 (11)	0.0009 (10)	0.0039 (11)
C19	0.0176 (13)	0.0259 (12)	0.0211 (13)	0.0003 (10)	−0.0006 (10)	−0.0037 (10)
C20	0.0247 (15)	0.0485 (17)	0.0162 (14)	−0.0050 (13)	−0.0026 (11)	0.0065 (12)
C21	0.0221 (14)	0.0406 (15)	0.0227 (15)	−0.0054 (12)	0.0014 (11)	0.0063 (12)

Geometric parameters (Å, º)

Gd1—O3	2.307 (2)	C3—C4	1.391 (4)
Gd1—O4^i	2.3444 (19)	C3—H3	0.9300
Gd1—O5	2.3509 (16)	C4—C5	1.394 (4)
Gd1—O6^ii	2.356 (2)	C4—H4	0.9300
Gd1—O2	2.4672 (18)	C5—C6	1.394 (4)
Gd1—O1	2.4720 (18)	C6—C7	1.387 (4)
Gd1—O7	2.5260 (19)	C6—H6	0.9300
Gd1—N3^iii	2.670 (2)	C7—H7	0.9300
O1—C1	1.272 (3)	C8—C9	1.492 (3)
O2—C1	1.278 (3)	C9—C10	1.395 (4)
O3—C8	1.258 (3)	C9—C14	1.397 (4)
O4—C8	1.265 (3)	C10—C11	1.383 (4)
O4—Gd1^i	2.3444 (18)	C10—H10	0.9300
O5—C15	1.261 (3)	C11—C12	1.382 (4)
O6—C15	1.268 (3)	C11—H11	0.9300
O6—Gd1^ii	2.356 (2)	C12—C13	1.399 (4)
O7—H1W	0.850 (10)	C13—C14	1.383 (4)
O7—H2W	0.850 (10)	C13—H13	0.9300
N1—C5	1.411 (3)	C14—H14	0.9300
N1—H1A	0.856 (10)	C15—C16	1.497 (3)
N1—H1B	0.854 (10)	C16—C17	1.391 (4)
N2—C12	1.399 (4)	C16—C21	1.396 (4)
N2—H2A	0.85 (3)	C17—C18	1.385 (3)
N2—H2B	0.853 (10)	C17—H17	0.9300
N3—C19	1.424 (3)	C18—C19	1.396 (4)
N3—Gd1^iii	2.670 (2)	C18—H18	0.9300
N3—H3A	0.9000	C19—C20	1.390 (4)
N3—H3B	0.9000	C20—C21	1.384 (4)
C1—C2	1.489 (3)	C20—H20	0.9300
C2—C7	1.393 (4)	C21—H21	0.9300
C2—C3	1.396 (4)
O3—Gd1—O4^i	103.75 (7)	C4—C3—H3	119.6
O3—Gd1—O5	93.03 (7)	C2—C3—H3	119.6
O4^i—Gd1—O5	143.63 (7)	C3—C4—C5	120.2 (3)
O3—Gd1—O6^ii	148.19 (7)	C3—C4—H4	119.9
O4^i—Gd1—O6^ii	88.98 (7)	C5—C4—H4	119.9
O5—Gd1—O6^ii	93.42 (7)	C6—C5—C4	119.1 (2)
O3—Gd1—O2	77.25 (7)	C6—C5—N1	120.5 (3)
O4^i—Gd1—O2	88.13 (7)	C4—C5—N1	120.4 (3)
O5—Gd1—O2	127.37 (6)	C7—C6—C5	120.6 (3)
O6^ii—Gd1—O2	74.13 (7)	C7—C6—H6	119.7
O3—Gd1—O1	79.53 (7)	C5—C6—H6	119.7
O4^i—Gd1—O1	140.00 (7)	C6—C7—C2	120.5 (3)
O5—Gd1—O1	74.23 (6)	C6—C7—H7	119.7
O6^ii—Gd1—O1	72.38 (7)	C2—C7—H7	119.7
O2—Gd1—O1	53.17 (6)	O3—C8—O4	122.3 (2)
O3—Gd1—O7	138.12 (7)	O3—C8—C9	119.3 (2)
O4^i—Gd1—O7	70.63 (7)	O4—C8—C9	118.4 (2)
O5—Gd1—O7	75.33 (6)	C10—C9—C14	118.2 (2)
O6^ii—Gd1—O7	73.51 (6)	C10—C9—C8	121.6 (2)
O2—Gd1—O7	141.27 (7)	C14—C9—C8	120.1 (2)
O1—Gd1—O7	132.12 (6)	C11—C10—C9	120.9 (3)
O3—Gd1—N3^iii	69.51 (7)	C11—C10—H10	119.6
O4^i—Gd1—N3^iii	74.94 (7)	C9—C10—H10	119.6
O5—Gd1—N3^iii	81.37 (7)	C12—C11—C10	120.8 (3)
O6^ii—Gd1—N3^iii	142.29 (7)	C12—C11—H11	119.6
O2—Gd1—N3^iii	137.27 (7)	C10—C11—H11	119.6
O1—Gd1—N3^iii	139.19 (7)	C11—C12—N2	121.6 (3)
O7—Gd1—N3^iii	69.02 (7)	C11—C12—C13	118.9 (3)
N3^iii—Gd1—C1	145.25 (8)	N2—C12—C13	119.4 (3)
C1—O1—Gd1	93.15 (15)	C14—C13—C12	120.2 (3)
C1—O2—Gd1	93.22 (14)	C14—C13—H13	119.9
C8—O3—Gd1	150.08 (18)	C12—C13—H13	119.9
C8—O4—Gd1^i	125.00 (17)	C13—C14—C9	120.9 (3)
C15—O5—Gd1	137.26 (17)	C13—C14—H14	119.5
C15—O6—Gd1^ii	145.42 (17)	C9—C14—H14	119.5
Gd1—O7—H1W	107.3 (19)	O5—C15—O6	122.8 (2)
Gd1—O7—H2W	118.0 (19)	O5—C15—C16	118.7 (2)
H1W—O7—H2W	112 (2)	O6—C15—C16	118.5 (2)
C5—N1—H1A	114 (2)	C17—C16—C21	119.0 (2)
C5—N1—H1B	111 (2)	C17—C16—C15	120.5 (2)
H1A—N1—H1B	115 (2)	C21—C16—C15	120.4 (2)
C12—N2—H2A	115 (3)	C18—C17—C16	120.7 (2)
C12—N2—H2B	116 (3)	C18—C17—H17	119.7
H2A—N2—H2B	119 (2)	C16—C17—H17	119.7
C19—N3—Gd1^iii	118.29 (15)	C17—C18—C19	120.1 (3)
C19—N3—H3A	107.7	C17—C18—H18	120.0
Gd1^iii—N3—H3A	107.7	C19—C18—H18	120.0
C19—N3—H3B	107.7	C20—C19—C18	119.3 (2)
Gd1^iii—N3—H3B	107.7	C20—C19—N3	120.7 (2)
H3A—N3—H3B	107.1	C18—C19—N3	119.9 (2)
O1—C1—O2	120.2 (2)	C21—C20—C19	120.5 (2)
O1—C1—C2	119.7 (2)	C21—C20—H20	119.7
O2—C1—C2	120.1 (2)	C19—C20—H20	119.7
C7—C2—C3	118.9 (2)	C20—C21—C16	120.3 (3)
C7—C2—C1	121.2 (2)	C20—C21—H21	119.8
C3—C2—C1	119.9 (2)	C16—C21—H21	119.8
C4—C3—C2	120.7 (3)
O3—Gd1—O1—C1	−79.04 (17)	C4—C5—C6—C7	−0.3 (5)
O4^i—Gd1—O1—C1	19.9 (2)	N1—C5—C6—C7	179.1 (3)
O5—Gd1—O1—C1	−175.24 (18)	C5—C6—C7—C2	−0.2 (5)
O6^ii—Gd1—O1—C1	85.87 (17)	C3—C2—C7—C6	0.6 (5)
O2—Gd1—O1—C1	2.80 (16)	C1—C2—C7—C6	179.3 (3)
O7—Gd1—O1—C1	132.36 (16)	Gd1—O3—C8—O4	103.6 (4)
N3^iii—Gd1—O1—C1	−119.68 (17)	Gd1—O3—C8—C9	−75.6 (4)
O3—Gd1—O2—C1	83.58 (17)	Gd1^i—O4—C8—O3	−1.7 (4)
O4^i—Gd1—O2—C1	−171.88 (17)	Gd1^i—O4—C8—C9	177.60 (17)
O5—Gd1—O2—C1	−0.4 (2)	O3—C8—C9—C10	170.3 (3)
O6^ii—Gd1—O2—C1	−82.41 (17)	O4—C8—C9—C10	−9.0 (4)
O1—Gd1—O2—C1	−2.79 (16)	O3—C8—C9—C14	−5.9 (4)
O7—Gd1—O2—C1	−116.71 (17)	O4—C8—C9—C14	174.8 (3)
N3^iii—Gd1—O2—C1	122.86 (17)	C14—C9—C10—C11	2.2 (5)
O4^i—Gd1—O3—C8	−111.8 (3)	C8—C9—C10—C11	−174.2 (3)
O5—Gd1—O3—C8	100.7 (3)	C9—C10—C11—C12	−1.5 (5)
O6^ii—Gd1—O3—C8	−0.7 (4)	C10—C11—C12—N2	178.0 (3)
O2—Gd1—O3—C8	−27.0 (3)	C10—C11—C12—C13	−1.1 (5)
O1—Gd1—O3—C8	27.4 (3)	C11—C12—C13—C14	3.0 (5)
O7—Gd1—O3—C8	172.0 (3)	N2—C12—C13—C14	−176.1 (3)
N3^iii—Gd1—O3—C8	−179.7 (4)	C12—C13—C14—C9	−2.4 (5)
C1—Gd1—O3—C8	0.4 (3)	C10—C9—C14—C13	−0.2 (5)
O3—Gd1—O5—C15	167.3 (2)	C8—C9—C14—C13	176.2 (3)
O4^i—Gd1—O5—C15	49.1 (3)	Gd1—O5—C15—O6	11.2 (4)
O6^ii—Gd1—O5—C15	−43.8 (2)	Gd1—O5—C15—C16	−167.67 (17)
O2—Gd1—O5—C15	−116.4 (2)	Gd1^ii—O6—C15—O5	89.9 (3)
O1—Gd1—O5—C15	−114.4 (3)	Gd1^ii—O6—C15—C16	−91.2 (3)
O7—Gd1—O5—C15	28.1 (2)	O5—C15—C16—C17	−5.8 (4)
N3^iii—Gd1—O5—C15	98.6 (2)	O6—C15—C16—C17	175.3 (2)
C1—Gd1—O5—C15	−116.6 (2)	O5—C15—C16—C21	171.9 (2)
Gd1—O1—C1—O2	−5.0 (3)	O6—C15—C16—C21	−7.0 (4)
Gd1—O1—C1—C2	173.9 (2)	C21—C16—C17—C18	0.5 (4)
Gd1—O2—C1—O1	5.0 (3)	C15—C16—C17—C18	178.2 (2)
Gd1—O2—C1—C2	−173.9 (2)	C16—C17—C18—C19	−2.1 (4)
O1—C1—C2—C7	160.3 (3)	C17—C18—C19—C20	2.1 (4)
O2—C1—C2—C7	−20.8 (4)	C17—C18—C19—N3	−174.1 (2)
O1—C1—C2—C3	−21.0 (4)	Gd1^iii—N3—C19—C20	−92.2 (3)
O2—C1—C2—C3	157.9 (3)	Gd1^iii—N3—C19—C18	84.0 (3)
C7—C2—C3—C4	−0.7 (5)	C18—C19—C20—C21	−0.5 (4)
C1—C2—C3—C4	−179.4 (3)	N3—C19—C20—C21	175.7 (3)
C2—C3—C4—C5	0.2 (5)	C19—C20—C21—C16	−1.2 (4)
C3—C4—C5—C6	0.3 (5)	C17—C16—C21—C20	1.2 (4)
C3—C4—C5—N1	−179.1 (3)	C15—C16—C21—C20	−176.5 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1W···O1^ii	0.85 (1)	2.58 (2)	3.184 (3)	129 (2)
O7—H1W···O6	0.85 (1)	2.00 (1)	2.786 (3)	153 (3)
N3—H3B···O2^iv	0.90	2.04	2.924 (3)	168
N3—H3A···N2^v	0.90	2.48	3.374 (4)	175
O7—H2W···N1^vi	0.85 (1)	2.09 (2)	2.892 (3)	158 (2)
N2—H2A···O7^vii	0.85 (3)	2.36 (2)	3.135 (4)	151 (4)
N1—H1A···O1^viii	0.86 (1)	2.23 (2)	2.985 (3)	147 (3)

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