Diaqua­azido­(3,5-diamino­benzoato-κN)(1,10-phenanthroline-κ²N,N′)zinc(II) monohydrate

The reaction of 3,5-diamino­benzoic acid, 1,10-phenanthroline, NaN₃ and Zn^II in basic aqueous solution gave rise to the title compound, [Zn(C₇H₇N₂O₂)(N₃)(C₁₂H₈N₂)(H₂O)₂]·H₂O. The Zn^II atom is six-coordinate with a distorted octa­hedral geometry. The two aqua ligands are in cis positions and the 3,5-diamino­benzoate ligand binds to the central Zn atom through one of its amino groups.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.025
• wR factor = 0.067
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N3     -   N4      ..       7.20 su

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   N5      ..       6.57 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N3
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1WB   ..  N4      ..       2.66 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Diaquaazido(3,5-diaminobenzoato-κN)(1,10-phenanthroline-κ²N,N')zinc(II) monohydrate

Crystal data

[Zn(C7H7N2O2)(N3)(C12H8N2)(H2O)2]·H2O	Z = 2
Mr = 492.80	F(000) = 508
Triclinic, P1	Dx = 1.584 Mg m^−3
a = 7.8039 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1720 (2) Å	Cell parameters from 5973 reflections
c = 13.4728 (2) Å	θ = 2.7–27.5°
α = 81.959 (1)°	µ = 1.24 mm^−1
β = 85.029 (1)°	T = 293 K
γ = 77.786 (1)°	Block, colourless
V = 1033.20 (3) Å^3	0.30 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	3629 independent reflections
Radiation source: fine-focus sealed tube	3307 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.708, Tmax = 0.827	k = −12→12
10775 measured reflections	l = −16→15

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 0.2809P] where P = (Fo^2 + 2Fc^2)/3
3629 reflections	(Δ/σ)max = 0.002
318 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.33 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
Zn1	0.96446 (3)	0.18279 (2)	0.776106 (16)	0.02717 (9)
C1	1.2251 (3)	−0.0404 (2)	0.66870 (19)	0.0461 (6)
H1	1.2418	−0.0861	0.7330	0.055*
C2	1.3202 (3)	−0.0982 (3)	0.5881 (2)	0.0554 (7)
H2	1.3988	−0.1806	0.5990	0.066*
C3	1.2979 (3)	−0.0339 (3)	0.4939 (2)	0.0530 (6)
H3	1.3597	−0.0725	0.4393	0.064*
C4	1.1805 (3)	0.0917 (2)	0.47906 (17)	0.0439 (5)
C5	1.1482 (4)	0.1665 (3)	0.38247 (18)	0.0575 (7)
H5	1.2105	0.1339	0.3259	0.069*
C6	1.0291 (4)	0.2833 (3)	0.37196 (18)	0.0579 (7)
H6	1.0096	0.3295	0.3080	0.070*
C7	0.9315 (3)	0.3384 (2)	0.45701 (16)	0.0425 (5)
C8	0.8041 (3)	0.4586 (3)	0.44954 (18)	0.0504 (6)
H8	0.7768	0.5060	0.3869	0.060*
C9	0.7209 (3)	0.5053 (2)	0.53377 (19)	0.0488 (6)
H9	0.6355	0.5846	0.5293	0.059*
C10	0.7644 (3)	0.4333 (2)	0.62807 (17)	0.0417 (5)
H10	0.7083	0.4677	0.6855	0.050*
C11	0.9646 (3)	0.2700 (2)	0.55399 (14)	0.0312 (4)
C12	1.0892 (3)	0.1430 (2)	0.56459 (15)	0.0318 (4)
C13	0.7330 (2)	0.40946 (17)	0.89294 (13)	0.0232 (4)
C14	0.8003 (2)	0.52348 (18)	0.89672 (13)	0.0248 (4)
H14	0.9174	0.5153	0.9098	0.030*
C15	0.6911 (2)	0.65102 (17)	0.88075 (13)	0.0243 (4)
C16	0.5173 (2)	0.66250 (18)	0.85925 (14)	0.0267 (4)
H16	0.4458	0.7480	0.8470	0.032*
C17	0.4488 (2)	0.54726 (19)	0.85587 (14)	0.0262 (4)
C18	0.5580 (2)	0.42029 (18)	0.87356 (14)	0.0263 (4)
H18	0.5140	0.3424	0.8724	0.032*
C19	0.7624 (2)	0.77614 (18)	0.88756 (14)	0.0263 (4)
H7A	0.245 (3)	0.490 (3)	0.8389 (19)	0.045 (7)*
H7B	0.203 (3)	0.626 (3)	0.8457 (18)	0.044 (7)*
H1WA	0.712 (3)	0.045 (3)	0.797 (2)	0.044 (8)*
H9WA	0.325 (3)	0.989 (3)	1.0160 (19)	0.046 (8)*
H1WB	0.647 (4)	0.146 (3)	0.739 (2)	0.052 (8)*
H2WB	0.997 (3)	−0.071 (3)	0.8836 (18)	0.049 (7)*
H9WB	0.420 (4)	0.919 (3)	0.947 (2)	0.055 (8)*
N1	1.1115 (2)	0.07697 (16)	0.65801 (13)	0.0328 (4)
N2	0.8824 (2)	0.31810 (16)	0.63837 (12)	0.0313 (4)
N3	1.1850 (3)	0.2732 (2)	0.79167 (16)	0.0485 (5)
N4	1.3078 (2)	0.25850 (17)	0.73405 (15)	0.0380 (4)
N5	1.4276 (2)	0.2503 (2)	0.67590 (16)	0.0524 (5)
N6	0.8446 (2)	0.27711 (14)	0.90573 (12)	0.0257 (3)
H6A	0.7811	0.2206	0.9415	0.031*
H6B	0.9317	0.2818	0.9439	0.031*
N7	0.2765 (2)	0.5593 (2)	0.83058 (16)	0.0391 (4)
O1	0.7370 (2)	0.10497 (18)	0.76125 (13)	0.0366 (4)
O2	1.03315 (19)	0.00529 (14)	0.87731 (11)	0.0344 (3)
H2WA	1.1274	0.0042	0.9003	0.052*
O3	0.92316 (18)	0.76468 (14)	0.89555 (13)	0.0420 (4)
O4	0.65351 (17)	0.88859 (12)	0.88359 (11)	0.0334 (3)
O9	0.3255 (2)	0.93507 (16)	0.97908 (13)	0.0353 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02818 (13)	0.02190 (13)	0.03021 (13)	−0.00462 (9)	0.00070 (9)	−0.00128 (9)
C1	0.0420 (13)	0.0378 (12)	0.0541 (14)	0.0003 (10)	0.0016 (11)	−0.0067 (11)
C2	0.0450 (14)	0.0425 (14)	0.0757 (19)	0.0013 (11)	0.0088 (13)	−0.0205 (13)
C3	0.0470 (14)	0.0594 (16)	0.0583 (16)	−0.0140 (12)	0.0141 (12)	−0.0320 (13)
C4	0.0444 (13)	0.0534 (14)	0.0416 (13)	−0.0214 (11)	0.0053 (10)	−0.0195 (11)
C5	0.0720 (18)	0.0720 (19)	0.0348 (13)	−0.0241 (15)	0.0081 (12)	−0.0204 (12)
C6	0.0807 (19)	0.0728 (19)	0.0261 (12)	−0.0294 (16)	−0.0035 (12)	−0.0046 (11)
C7	0.0512 (14)	0.0473 (13)	0.0342 (11)	−0.0230 (11)	−0.0071 (10)	−0.0001 (10)
C8	0.0610 (16)	0.0504 (14)	0.0397 (13)	−0.0175 (12)	−0.0182 (12)	0.0138 (11)
C9	0.0467 (14)	0.0392 (13)	0.0553 (15)	−0.0043 (11)	−0.0119 (11)	0.0109 (11)
C10	0.0420 (12)	0.0355 (12)	0.0435 (12)	−0.0051 (10)	0.0011 (10)	0.0032 (10)
C11	0.0341 (11)	0.0352 (11)	0.0283 (10)	−0.0177 (9)	−0.0019 (8)	−0.0016 (8)
C12	0.0312 (10)	0.0355 (11)	0.0337 (11)	−0.0163 (9)	0.0023 (8)	−0.0092 (9)
C13	0.0278 (9)	0.0184 (9)	0.0229 (9)	−0.0038 (7)	0.0013 (7)	−0.0037 (7)
C14	0.0227 (9)	0.0233 (9)	0.0295 (10)	−0.0070 (7)	−0.0008 (7)	−0.0034 (7)
C15	0.0278 (10)	0.0208 (9)	0.0250 (9)	−0.0068 (7)	0.0005 (7)	−0.0039 (7)
C16	0.0288 (10)	0.0202 (9)	0.0303 (10)	−0.0014 (7)	−0.0031 (8)	−0.0050 (7)
C17	0.0241 (9)	0.0290 (10)	0.0269 (9)	−0.0056 (8)	−0.0022 (7)	−0.0070 (8)
C18	0.0288 (10)	0.0230 (9)	0.0304 (10)	−0.0115 (8)	0.0005 (8)	−0.0066 (8)
C19	0.0292 (10)	0.0208 (9)	0.0294 (10)	−0.0073 (8)	0.0027 (8)	−0.0045 (7)
N1	0.0314 (9)	0.0297 (9)	0.0373 (9)	−0.0060 (7)	0.0012 (7)	−0.0063 (7)
N2	0.0313 (9)	0.0290 (9)	0.0321 (9)	−0.0080 (7)	0.0001 (7)	0.0028 (7)
N3	0.0377 (11)	0.0508 (12)	0.0651 (13)	−0.0221 (9)	0.0095 (10)	−0.0222 (10)
N4	0.0314 (10)	0.0312 (9)	0.0534 (11)	−0.0084 (7)	−0.0116 (9)	−0.0034 (8)
N5	0.0295 (10)	0.0637 (14)	0.0586 (13)	−0.0067 (9)	0.0007 (10)	0.0041 (10)
N6	0.0279 (8)	0.0171 (7)	0.0324 (8)	−0.0054 (6)	−0.0037 (7)	−0.0014 (6)
N7	0.0269 (9)	0.0319 (10)	0.0618 (13)	−0.0048 (9)	−0.0104 (8)	−0.0138 (9)
O1	0.0326 (9)	0.0336 (9)	0.0436 (9)	−0.0115 (7)	−0.0077 (7)	0.0065 (7)
O2	0.0359 (8)	0.0242 (7)	0.0444 (9)	−0.0106 (6)	−0.0126 (6)	0.0046 (6)
O3	0.0293 (8)	0.0248 (7)	0.0748 (11)	−0.0086 (6)	−0.0068 (7)	−0.0093 (7)
O4	0.0305 (7)	0.0181 (7)	0.0513 (9)	−0.0053 (6)	0.0030 (6)	−0.0059 (6)
O9	0.0267 (8)	0.0367 (8)	0.0460 (9)	−0.0100 (6)	0.0018 (7)	−0.0139 (7)

Geometric parameters (Å, º)

Zn1—O2	2.1060 (13)	C11—C12	1.441 (3)
Zn1—O1	2.1255 (15)	C12—N1	1.348 (3)
Zn1—N3	2.1539 (18)	C13—C14	1.380 (2)
Zn1—N1	2.1558 (16)	C13—C18	1.391 (3)
Zn1—N6	2.1568 (15)	C13—N6	1.437 (2)
Zn1—N2	2.2061 (16)	C14—C15	1.393 (3)
C1—N1	1.326 (3)	C14—H14	0.9300
C1—C2	1.389 (3)	C15—C16	1.389 (3)
C1—H1	0.9300	C15—C19	1.510 (2)
C2—C3	1.352 (4)	C16—C17	1.395 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.406 (4)	C17—C18	1.391 (3)
C3—H3	0.9300	C17—N7	1.391 (3)
C4—C12	1.406 (3)	C18—H18	0.9300
C4—C5	1.426 (4)	C19—O3	1.248 (2)
C5—C6	1.343 (4)	C19—O4	1.270 (2)
C5—H5	0.9300	N3—N4	1.177 (3)
C6—C7	1.434 (4)	N4—N5	1.163 (3)
C6—H6	0.9300	N6—H6A	0.9000
C7—C8	1.401 (3)	N6—H6B	0.9000
C7—C11	1.409 (3)	N7—H7A	0.79 (3)
C8—C9	1.352 (4)	N7—H7B	0.83 (3)
C8—H8	0.9300	O1—H1WA	0.77 (3)
C9—C10	1.406 (3)	O1—H1WB	0.80 (3)
C9—H9	0.9300	O2—H2WB	0.87 (3)
C10—N2	1.326 (3)	O2—H2WA	0.8200
C10—H10	0.9300	O9—H9WA	0.79 (3)
C11—N2	1.356 (3)	O9—H9WB	0.82 (3)
O2—Zn1—O1	83.93 (6)	N1—C12—C4	122.5 (2)
O2—Zn1—N3	98.48 (7)	N1—C12—C11	117.54 (17)
O1—Zn1—N3	176.63 (7)	C4—C12—C11	119.91 (19)
O2—Zn1—N1	88.90 (6)	C14—C13—C18	120.90 (16)
O1—Zn1—N1	92.80 (6)	C14—C13—N6	120.32 (16)
N3—Zn1—N1	89.62 (7)	C18—C13—N6	118.75 (16)
O2—Zn1—N6	85.89 (6)	C13—C14—C15	119.34 (17)
O1—Zn1—N6	91.55 (6)	C13—C14—H14	120.3
N3—Zn1—N6	86.28 (7)	C15—C14—H14	120.3
N1—Zn1—N6	172.82 (6)	C16—C15—C14	119.98 (17)
O2—Zn1—N2	160.85 (6)	C16—C15—C19	120.34 (16)
O1—Zn1—N2	84.22 (6)	C14—C15—C19	119.68 (16)
N3—Zn1—N2	94.06 (7)	C15—C16—C17	120.74 (17)
N1—Zn1—N2	76.71 (6)	C15—C16—H16	119.6
N6—Zn1—N2	109.43 (6)	C17—C16—H16	119.6
N1—C1—C2	122.9 (2)	C18—C17—N7	120.55 (18)
N1—C1—H1	118.5	C18—C17—C16	118.84 (17)
C2—C1—H1	118.5	N7—C17—C16	120.54 (18)
C3—C2—C1	119.7 (2)	C13—C18—C17	120.18 (17)
C3—C2—H2	120.2	C13—C18—H18	119.9
C1—C2—H2	120.2	C17—C18—H18	119.9
C2—C3—C4	119.4 (2)	O3—C19—O4	123.58 (17)
C2—C3—H3	120.3	O3—C19—C15	119.11 (16)
C4—C3—H3	120.3	O4—C19—C15	117.30 (16)
C12—C4—C3	117.4 (2)	C1—N1—C12	118.12 (18)
C12—C4—C5	119.4 (2)	C1—N1—Zn1	126.94 (15)
C3—C4—C5	123.3 (2)	C12—N1—Zn1	114.85 (13)
C6—C5—C4	121.0 (2)	C10—N2—C11	118.04 (18)
C6—C5—H5	119.5	C10—N2—Zn1	129.40 (14)
C4—C5—H5	119.5	C11—N2—Zn1	112.53 (13)
C5—C6—C7	121.5 (2)	N4—N3—Zn1	120.28 (16)
C5—C6—H6	119.2	N5—N4—N3	176.9 (2)
C7—C6—H6	119.2	C13—N6—Zn1	120.01 (11)
C8—C7—C11	117.4 (2)	C13—N6—H6A	107.3
C8—C7—C6	123.5 (2)	Zn1—N6—H6A	107.3
C11—C7—C6	119.1 (2)	C13—N6—H6B	107.3
C9—C8—C7	119.7 (2)	Zn1—N6—H6B	107.3
C9—C8—H8	120.1	H6A—N6—H6B	106.9
C7—C8—H8	120.1	C17—N7—H7A	113.3 (18)
C8—C9—C10	119.6 (2)	C17—N7—H7B	118.1 (17)
C8—C9—H9	120.2	H7A—N7—H7B	116 (2)
C10—C9—H9	120.2	Zn1—O1—H1WA	122.6 (19)
N2—C10—C9	122.6 (2)	Zn1—O1—H1WB	127.0 (19)
N2—C10—H10	118.7	H1WA—O1—H1WB	105 (3)
C9—C10—H10	118.7	Zn1—O2—H2WB	130.2 (17)
N2—C11—C7	122.68 (19)	Zn1—O2—H2WA	109.5
N2—C11—C12	118.27 (17)	H2WB—O2—H2WA	117.5
C7—C11—C12	119.05 (19)	H9WA—O9—H9WB	111 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7A···N3^i	0.79 (3)	2.52 (3)	3.260 (3)	157 (2)
N7—H7B···O3^i	0.83 (3)	2.43 (3)	3.223 (2)	160 (2)
O1—H1WA···O4^ii	0.77 (3)	1.95 (3)	2.719 (2)	178 (3)
O9—H9WA···O4^iii	0.79 (3)	2.00 (3)	2.788 (2)	174 (3)
O1—H1WB···N5^i	0.80 (3)	2.00 (3)	2.799 (3)	177 (3)
O1—H1WB···N4^i	0.80 (3)	2.66 (3)	3.410 (2)	159 (2)
O2—H2WB···O3^ii	0.87 (3)	1.86 (3)	2.7334 (19)	179 (2)
O9—H9WB···O4	0.82 (3)	1.93 (3)	2.742 (2)	174 (3)
N6—H6A···O9^iv	0.90	2.07	2.957 (2)	170
N6—H6B···O3^v	0.90	2.47	3.291 (2)	152
O2—H2WA···O9^vi	0.82	1.90	2.678 (2)	157

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