{2-[(1,5-Di­methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl­imino)­methyl]­phenoxy}acetic acid nitrate

The title compound, C₂₀H₂₀N₃O₄⁺.NO₃^-, has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The cations and anions form chains parallel to the a axis through intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.065
• wR factor = 0.198
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.97

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.00 Ratio
PLAT390_ALERT_3_B Deviating Methyl C19     X-C-H Bond Angle ......     120.00 Deg.
PLAT390_ALERT_3_B Deviating Methyl C20     X-C-H Bond Angle ......     121.10 Deg.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.42
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C17      =       5.55 su
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         N4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT351_ALERT_3_C Long    C-H Bond (0.96A)   C15    -   H11      =       1.16 Ang.
PLAT390_ALERT_3_C Deviating Methyl C20     X-C-H Bond Angle ......     118.00 Deg.
PLAT391_ALERT_3_C Deviating Methyl C19     H-C-H Bond Angle ......     100.00 Deg.
PLAT391_ALERT_3_C Deviating Methyl C19     H-C-H Bond Angle ......     101.00 Deg.
PLAT731_ALERT_1_C Bond    Calc     0.96(3), Rep   0.965(10) ......       3.00 su-Rat
              C20  -H19     1.555   1.555

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

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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

{2-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4- ylimino)methyl]phenoxy}acetic acid nitrate

Crystal data

C20H20N3O4^+·NO3^−	F(000) = 896
Mr = 428.40	Dx = 1.445 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.102 (3) Å	Cell parameters from 1434 reflections
b = 11.110 (5) Å	θ = 3.1–21.5°
c = 25.177 (10) Å	µ = 0.11 mm^−1
β = 97.608 (7)°	T = 298 K
V = 1969.1 (14) Å^3	Block, yellow
Z = 4	0.37 × 0.29 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3390 independent reflections
Radiation source: fine-focus sealed tube	1737 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.960, Tmax = 0.977	k = −13→11
9917 measured reflections	l = −29→29

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.198	All H-atom parameters refined
S = 0.89	w = 1/[σ^2(Fo^2) + (0.1199P)^2] where P = (Fo^2 + 2Fc^2)/3
3390 reflections	(Δ/σ)max < 0.001
360 parameters	Δρmax = 0.57 e Å^−3
12 restraints	Δρmin = −0.32 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
N1	0.8003 (4)	0.6942 (3)	0.33515 (11)	0.0466 (8)
N2	0.9547 (4)	0.6501 (3)	0.31210 (11)	0.0498 (8)
N3	0.9441 (5)	0.4397 (3)	0.41756 (12)	0.0445 (8)
N4	0.9560 (6)	0.1406 (4)	0.35655 (15)	0.0652 (10)
O1	0.6318 (4)	0.6292 (2)	0.40320 (10)	0.0599 (8)
O2	1.4450 (4)	0.3015 (3)	0.41444 (12)	0.0739 (9)
O3	1.5536 (5)	0.1141 (3)	0.43005 (13)	0.0768 (9)
O4	1.1514 (4)	0.2580 (2)	0.46914 (9)	0.0510 (7)
O5	0.8697 (6)	0.1055 (6)	0.39121 (18)	0.150 (2)
O6	0.9611 (12)	0.2446 (5)	0.34836 (17)	0.197 (3)
O7	1.0510 (11)	0.0851 (7)	0.3354 (2)	0.225 (4)
C1	0.7671 (5)	0.6185 (3)	0.37708 (13)	0.0451 (9)
C2	0.9165 (5)	0.5325 (3)	0.38003 (13)	0.0451 (9)
C3	1.0302 (5)	0.5570 (3)	0.34126 (13)	0.0430 (9)
C4	1.4363 (5)	0.2042 (4)	0.43469 (16)	0.0541 (10)
C5	1.2932 (6)	0.1686 (4)	0.47119 (19)	0.0574 (11)
C6	0.8462 (5)	0.4252 (4)	0.45742 (14)	0.0465 (9)
C7	0.8697 (5)	0.3318 (3)	0.49701 (13)	0.0419 (9)
C8	1.0161 (5)	0.2442 (3)	0.50208 (13)	0.0437 (9)
C9	1.0169 (6)	0.1551 (4)	0.53996 (15)	0.0498 (10)
C10	0.8770 (6)	0.1523 (4)	0.57389 (15)	0.0535 (11)
C11	0.7376 (6)	0.2387 (4)	0.57059 (15)	0.0549 (10)
C12	0.7341 (6)	0.3272 (4)	0.53273 (14)	0.0499 (10)
C13	0.6642 (5)	0.7714 (3)	0.30560 (14)	0.0453 (9)
C14	0.5921 (6)	0.8653 (4)	0.33272 (17)	0.0543 (11)
C15	0.4532 (6)	0.9391 (4)	0.30598 (18)	0.0633 (11)
C16	0.3963 (7)	0.9205 (5)	0.2516 (2)	0.0661 (13)
C17	0.4712 (6)	0.8292 (4)	0.22490 (17)	0.0576 (11)
C18	0.6053 (6)	0.7536 (4)	0.25201 (16)	0.0536 (10)
C19	1.0604 (6)	0.7358 (4)	0.28274 (17)	0.0607 (11)
C20	1.2069 (6)	0.4971 (4)	0.32962 (18)	0.0627 (11)
H1	1.640 (6)	0.135 (3)	0.4050 (15)	0.065 (12)*
H2	1.237 (5)	0.083 (4)	0.4624 (13)	0.054 (10)*
H3	1.346 (6)	0.159 (4)	0.5056 (18)	0.075 (14)*
H4	1.024 (5)	0.393 (3)	0.4138 (13)	0.035 (11)*
H5	0.758 (4)	0.485 (3)	0.4632 (11)	0.027 (8)*
H6	1.110 (5)	0.094 (3)	0.5422 (13)	0.044 (10)*
H7	0.880 (4)	0.089 (3)	0.5971 (11)	0.024 (8)*
H8	0.641 (6)	0.242 (4)	0.5956 (16)	0.067 (11)*
H9	0.646 (6)	0.399 (4)	0.5345 (14)	0.061 (11)*
H10	0.629 (6)	0.877 (3)	0.3678 (16)	0.062 (12)*
H11	0.402 (6)	1.013 (4)	0.3332 (17)	0.089 (14)*
H12	0.314 (6)	0.972 (4)	0.2355 (17)	0.075 (15)*
H13	0.433 (5)	0.814 (3)	0.1862 (14)	0.041 (9)*
H14	0.665 (5)	0.695 (4)	0.2313 (15)	0.057 (11)*
H15	1.077 (6)	0.8163 (18)	0.2980 (14)	0.109 (19)*
H16	1.015 (5)	0.756 (3)	0.2458 (6)	0.077 (13)*
H17	1.192 (3)	0.714 (4)	0.2806 (16)	0.12 (2)*
H18	1.219 (5)	0.478 (3)	0.2927 (6)	0.086 (14)*
H19	1.330 (3)	0.531 (3)	0.3419 (14)	0.102 (17)*
H20	1.210 (6)	0.4192 (18)	0.3464 (14)	0.113 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0422 (17)	0.0525 (19)	0.0473 (17)	0.0042 (14)	0.0140 (14)	0.0076 (15)
N2	0.0440 (18)	0.061 (2)	0.0452 (17)	−0.0023 (16)	0.0093 (14)	0.0048 (16)
N3	0.0431 (19)	0.0453 (19)	0.0457 (18)	0.0051 (16)	0.0087 (15)	0.0044 (15)
N4	0.070 (3)	0.061 (3)	0.067 (2)	0.022 (2)	0.019 (2)	0.003 (2)
O1	0.0544 (17)	0.0679 (19)	0.0617 (16)	0.0103 (14)	0.0238 (14)	0.0161 (14)
O2	0.0600 (19)	0.086 (2)	0.079 (2)	0.0105 (16)	0.0211 (16)	0.0222 (18)
O3	0.063 (2)	0.078 (2)	0.094 (2)	0.0152 (17)	0.0290 (18)	−0.0005 (19)
O4	0.0485 (15)	0.0554 (16)	0.0504 (14)	0.0042 (13)	0.0113 (12)	0.0077 (12)
O5	0.083 (3)	0.265 (6)	0.109 (3)	−0.031 (4)	0.043 (3)	−0.016 (4)
O6	0.414 (10)	0.086 (3)	0.077 (3)	−0.010 (4)	−0.020 (4)	−0.009 (3)
O7	0.311 (9)	0.243 (7)	0.148 (4)	0.178 (7)	0.134 (5)	0.096 (4)
C1	0.042 (2)	0.052 (2)	0.0414 (19)	−0.0026 (18)	0.0056 (16)	0.0060 (18)
C2	0.043 (2)	0.053 (2)	0.0409 (19)	−0.0040 (17)	0.0085 (17)	0.0033 (18)
C3	0.041 (2)	0.047 (2)	0.0400 (19)	0.0034 (17)	0.0026 (16)	−0.0037 (17)
C4	0.041 (2)	0.069 (3)	0.052 (2)	0.005 (2)	0.0041 (18)	0.003 (2)
C5	0.053 (3)	0.061 (3)	0.059 (3)	0.005 (2)	0.009 (2)	0.006 (2)
C6	0.048 (2)	0.048 (2)	0.045 (2)	0.0014 (19)	0.0083 (18)	0.0004 (18)
C7	0.045 (2)	0.044 (2)	0.0363 (18)	−0.0024 (17)	0.0030 (16)	0.0002 (16)
C8	0.042 (2)	0.053 (2)	0.0369 (18)	−0.0035 (17)	0.0067 (16)	−0.0033 (17)
C9	0.051 (2)	0.051 (2)	0.047 (2)	0.000 (2)	0.0046 (19)	0.0005 (19)
C10	0.069 (3)	0.051 (2)	0.041 (2)	−0.005 (2)	0.011 (2)	0.007 (2)
C11	0.054 (2)	0.064 (3)	0.048 (2)	0.001 (2)	0.0155 (19)	0.002 (2)
C12	0.046 (2)	0.058 (3)	0.046 (2)	−0.003 (2)	0.0086 (18)	0.000 (2)
C13	0.045 (2)	0.045 (2)	0.047 (2)	0.0003 (18)	0.0083 (17)	0.0076 (18)
C14	0.063 (3)	0.053 (3)	0.045 (2)	0.003 (2)	−0.001 (2)	0.007 (2)
C15	0.068 (3)	0.057 (3)	0.066 (3)	0.006 (2)	0.014 (2)	0.009 (2)
C16	0.049 (3)	0.068 (3)	0.078 (3)	−0.004 (2)	−0.003 (2)	0.026 (3)
C17	0.055 (3)	0.068 (3)	0.049 (2)	−0.007 (2)	0.001 (2)	0.008 (2)
C18	0.056 (2)	0.056 (3)	0.049 (2)	−0.003 (2)	0.007 (2)	−0.001 (2)
C19	0.062 (3)	0.067 (3)	0.058 (3)	−0.007 (2)	0.025 (2)	0.016 (2)
C20	0.049 (3)	0.077 (3)	0.065 (3)	0.012 (2)	0.018 (2)	0.005 (2)

Geometric parameters (Å, º)

N1—C1	1.394 (4)	C7—C8	1.417 (5)
N1—N2	1.395 (4)	C8—C9	1.375 (5)
N1—C13	1.426 (4)	C9—C10	1.394 (5)
N2—C3	1.339 (4)	C9—H6	0.94 (4)
N2—C19	1.471 (5)	C10—C11	1.374 (6)
N3—C6	1.304 (5)	C10—H7	0.91 (3)
N3—C2	1.394 (5)	C11—C12	1.367 (6)
N3—H4	0.79 (3)	C11—H8	0.99 (4)
N4—O7	1.103 (5)	C12—H9	1.01 (4)
N4—O6	1.174 (6)	C13—C18	1.373 (5)
N4—O5	1.196 (5)	C13—C14	1.382 (5)
O1—C1	1.240 (4)	C14—C15	1.387 (6)
O2—C4	1.201 (5)	C14—H10	0.90 (4)
O3—C4	1.317 (5)	C15—C16	1.392 (6)
O3—H1	0.96 (4)	C15—H11	1.16 (5)
O4—C8	1.358 (4)	C16—C17	1.362 (7)
O4—C5	1.412 (5)	C16—H12	0.88 (5)
C1—C2	1.422 (5)	C17—C18	1.381 (6)
C2—C3	1.374 (5)	C17—H13	0.99 (3)
C3—C20	1.484 (5)	C18—H14	0.96 (4)
C4—C5	1.510 (6)	C19—H15	0.973 (10)
C5—H2	1.04 (4)	C19—H16	0.970 (10)
C5—H3	0.90 (4)	C19—H17	0.972 (10)
C6—C7	1.433 (5)	C20—H18	0.969 (10)
C6—H5	0.94 (3)	C20—H19	0.965 (10)
C7—C12	1.403 (5)	C20—H20	0.962 (10)
C1—N1—N2	108.9 (3)	C8—C9—H6	120 (2)
C1—N1—C13	126.0 (3)	C10—C9—H6	120 (2)
N2—N1—C13	120.6 (3)	C11—C10—C9	120.9 (4)
C3—N2—N1	108.8 (3)	C11—C10—H7	122.0 (18)
C3—N2—C19	125.6 (3)	C9—C10—H7	117.0 (19)
N1—N2—C19	117.6 (3)	C12—C11—C10	119.4 (4)
C6—N3—C2	124.9 (3)	C12—C11—H8	118 (2)
C6—N3—H4	119 (2)	C10—C11—H8	123 (2)
C2—N3—H4	117 (2)	C11—C12—C7	121.5 (4)
O7—N4—O6	115.4 (6)	C11—C12—H9	119 (2)
O7—N4—O5	125.2 (6)	C7—C12—H9	119 (2)
O6—N4—O5	118.7 (6)	C18—C13—C14	120.7 (4)
C4—O3—H1	110 (2)	C18—C13—N1	121.5 (4)
C8—O4—C5	117.2 (3)	C14—C13—N1	117.8 (3)
O1—C1—N1	124.4 (3)	C13—C14—C15	119.5 (4)
O1—C1—C2	131.4 (3)	C13—C14—H10	121 (3)
N1—C1—C2	104.2 (3)	C15—C14—H10	119 (3)
C3—C2—N3	125.8 (3)	C14—C15—C16	119.0 (4)
C3—C2—C1	109.5 (3)	C14—C15—H11	113 (2)
N3—C2—C1	124.6 (3)	C16—C15—H11	128 (2)
N2—C3—C2	108.2 (3)	C17—C16—C15	121.0 (5)
N2—C3—C20	121.8 (3)	C17—C16—H12	123 (3)
C2—C3—C20	130.0 (4)	C15—C16—H12	116 (3)
O2—C4—O3	125.3 (4)	C16—C17—C18	119.9 (4)
O2—C4—C5	124.8 (4)	C16—C17—H13	123 (2)
O3—C4—C5	109.8 (4)	C18—C17—H13	118 (2)
O4—C5—C4	109.1 (4)	C13—C18—C17	119.9 (4)
O4—C5—H2	112 (2)	C13—C18—H14	122 (2)
C4—C5—H2	112 (2)	C17—C18—H14	118 (2)
O4—C5—H3	109 (3)	N2—C19—H15	116 (3)
C4—C5—H3	113 (3)	N2—C19—H16	121 (2)
H2—C5—H3	101 (3)	H15—C19—H16	99.7 (19)
N3—C6—C7	126.8 (4)	N2—C19—H17	115 (3)
N3—C6—H5	117.7 (18)	H15—C19—H17	101 (2)
C7—C6—H5	115.2 (18)	H16—C19—H17	102 (2)
C12—C7—C8	118.4 (3)	C3—C20—H18	118 (2)
C12—C7—C6	116.5 (3)	C3—C20—H19	121 (3)
C8—C7—C6	125.2 (3)	H18—C20—H19	102 (2)
O4—C8—C9	124.5 (3)	C3—C20—H20	107 (3)
O4—C8—C7	115.9 (3)	H18—C20—H20	103 (2)
C9—C8—C7	119.5 (3)	H19—C20—H20	104 (2)
C8—C9—C10	120.2 (4)
C1—N1—N2—C3	−6.0 (4)	N3—C6—C7—C8	5.7 (6)
C13—N1—N2—C3	−163.6 (3)	C5—O4—C8—C9	5.5 (5)
C1—N1—N2—C19	−156.7 (3)	C5—O4—C8—C7	−176.6 (3)
C13—N1—N2—C19	45.7 (5)	C12—C7—C8—O4	−175.3 (3)
N2—N1—C1—O1	−175.1 (3)	C6—C7—C8—O4	5.6 (5)
C13—N1—C1—O1	−19.0 (6)	C12—C7—C8—C9	2.7 (5)
N2—N1—C1—C2	3.8 (4)	C6—C7—C8—C9	−176.4 (4)
C13—N1—C1—C2	159.9 (3)	O4—C8—C9—C10	176.5 (3)
C6—N3—C2—C3	172.6 (4)	C7—C8—C9—C10	−1.3 (5)
C6—N3—C2—C1	−5.7 (6)	C8—C9—C10—C11	−0.7 (6)
O1—C1—C2—C3	178.4 (4)	C9—C10—C11—C12	1.4 (6)
N1—C1—C2—C3	−0.4 (4)	C10—C11—C12—C7	0.1 (6)
O1—C1—C2—N3	−3.0 (6)	C8—C7—C12—C11	−2.1 (5)
N1—C1—C2—N3	178.2 (3)	C6—C7—C12—C11	177.1 (4)
N1—N2—C3—C2	5.6 (4)	C1—N1—C13—C18	−114.8 (4)
C19—N2—C3—C2	153.4 (4)	N2—N1—C13—C18	38.7 (5)
N1—N2—C3—C20	−174.8 (3)	C1—N1—C13—C14	65.0 (5)
C19—N2—C3—C20	−27.0 (6)	N2—N1—C13—C14	−141.5 (4)
N3—C2—C3—N2	178.1 (3)	C18—C13—C14—C15	2.7 (6)
C1—C2—C3—N2	−3.3 (4)	N1—C13—C14—C15	−177.1 (3)
N3—C2—C3—C20	−1.4 (6)	C13—C14—C15—C16	−3.3 (6)
C1—C2—C3—C20	177.2 (4)	C14—C15—C16—C17	1.9 (6)
C8—O4—C5—C4	−176.3 (3)	C15—C16—C17—C18	0.1 (7)
O2—C4—C5—O4	11.4 (6)	C14—C13—C18—C17	−0.7 (6)
O3—C4—C5—O4	−170.9 (3)	N1—C13—C18—C17	179.1 (3)
C2—N3—C6—C7	−179.8 (3)	C16—C17—C18—C13	−0.7 (6)
N3—C6—C7—C12	−173.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O5^i	0.96 (4)	1.75 (4)	2.567 (5)	141 (3)
N3—H4···O4	0.79 (3)	2.16 (3)	2.724 (4)	129 (3)

Symmetry code: (i) x+1, y, z.