Ethyl 1-acetyl-3-amino-1H-pyrazole-4-carboxyl­ate, a tetra­gonal structure with Z′ = 4

Koziol, A.E.; Lis, T.; Kolodziejczyk, E.; Kusakiewicz-Dawid, A.; Rzeszotarska, B.

doi:10.1107/S1600536806029515

Ethyl 1-acetyl-3-amino-1H-pyrazole-4-carboxylate, a tetragonal structure with Z′ = 4

A. E. Koziol, T. Lis, E. Kolodziejczyk, A. Kusakiewicz-Dawid and B. Rzeszotarska

The title compound, C₈H₁₁N₃O₃, crystallizes with Z′ = 4. One pyrazole N atom is substituted and excluded from intermolecular contacts. The amine N, acetyl O and an ester O atom are involved in the formation of nearly planar molecular layers. The layers are perpendicular to the c axis, with an interlayer distance of 3.333 Å. The hydrogen-bonding patterns are similar for each molecule, i.e. intramolecular N—H

O, as well as intermolecular N—H

O and C—H

N(pyrazole), bonds are present.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029515/cs2018sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029515/cs2018Isup2.hkl Contains datablock I

CCDC reference: 620768

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.046
wR factor = 0.115
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.63 mm
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C2C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         40

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           37.48
           From the CIF: _reflns_number_total               7874
           From the CIF: _diffrn_reflns_limit_ max hkl   23.   27.   22.
           From the CIF: _diffrn_reflns_limit_ min hkl  -26.  -21.  -17.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   28.   28.   22.
           Calculated minimum hkl  -28.  -28.  -22.
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           37.48
           From the CIF: _reflns_number_total               7874
           Count of symmetry unique reflns        10324
           Completeness (_total/calc)             76.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).

Ethyl 1-acetyl-3-amino-1H-pyrazole-4-carboxylate top

Crystal data top

C₈H₁₁N₃O₃	D_x = 1.378 Mg m⁻³
M_r = 197.20	Melting point: 383 K K
Tetragonal, P4₃	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4cw	Cell parameters from 32167 reflections
a = 16.887 (6) Å	θ = 3.1–35.0°
c = 13.332 (5) Å	µ = 0.11 mm⁻¹
V = 3802 (2) Å³	T = 100 K
Z = 16	Prism, colourless
F(000) = 1664	0.63 × 0.52 × 0.35 mm

Data collection top

Kuma KM4 CCD area-detector diffractometer	7874 independent reflections
Radiation source: fine-focus sealed tube	6125 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 37.5°, θ_min = 3.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2001)	h = −26→23
T_min = 0.929, T_max = 0.963	k = −21→27
37699 measured reflections	l = −17→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.071P)²] where P = (F_o² + 2F_c²)/3
7874 reflections	(Δ/σ)_max < 0.001
513 parameters	Δρ_max = 0.48 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Special details top

Experimental. crystallization from DMF

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. The absolute structure Flack parameter is inconclusive for CHNO compound. Absolute structure not discussed.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.70036 (8)	0.52791 (8)	−0.02037 (10)	0.0147 (3)
N2A	0.78154 (8)	0.51636 (8)	−0.03002 (10)	0.0155 (3)
C3A	0.78984 (10)	0.43787 (10)	−0.03228 (11)	0.0152 (3)
N3A	0.86082 (8)	0.40294 (9)	−0.04468 (11)	0.0194 (3)
H3A1	0.9037	0.4321	−0.0516	0.023*
H3A2	0.8644	0.3510	−0.0458	0.023*
C4A	0.71427 (10)	0.39882 (10)	−0.02344 (12)	0.0148 (3)
C5A	0.65956 (10)	0.45906 (10)	−0.01628 (12)	0.0157 (3)
H5A	0.6038	0.4533	−0.0097	0.019*
C1A	0.66713 (10)	0.60456 (10)	−0.01792 (11)	0.0162 (3)
O1A	0.59496 (7)	0.61043 (8)	−0.01590 (10)	0.0226 (3)
C2A	0.72431 (10)	0.67128 (10)	−0.01700 (14)	0.0200 (3)
H2A1	0.7552	0.6708	−0.0792	0.030*
H2A2	0.7600	0.6657	0.0405	0.030*
H2A3	0.6954	0.7214	−0.0117	0.030*
C6A	0.69975 (10)	0.31378 (10)	−0.02540 (12)	0.0160 (3)
O6A	0.75112 (8)	0.26354 (7)	−0.02915 (11)	0.0243 (3)
O7A	0.62150 (7)	0.29713 (7)	−0.02309 (9)	0.0192 (2)
C7A	0.60000 (11)	0.21360 (10)	−0.02919 (14)	0.0207 (3)
H7A1	0.6149	0.1858	0.0334	0.025*
H7A2	0.6276	0.1880	−0.0861	0.025*
C8A	0.51138 (11)	0.21063 (12)	−0.04439 (14)	0.0256 (4)
H8A1	0.4943	0.1553	−0.0497	0.038*
H8A2	0.4975	0.2389	−0.1061	0.038*
H8A3	0.4849	0.2357	0.0128	0.038*
N1B	0.62325 (8)	−0.07923 (8)	−0.05593 (10)	0.0146 (3)
N2B	0.61118 (8)	−0.15995 (8)	−0.04260 (10)	0.0158 (3)
C3B	0.53251 (10)	−0.16743 (10)	−0.04173 (11)	0.0153 (3)
N3B	0.49696 (9)	−0.23804 (9)	−0.02556 (12)	0.0209 (3)
H3B1	0.5258	−0.2807	−0.0152	0.025*
H3B2	0.4450	−0.2414	−0.0254	0.025*
C4B	0.49370 (9)	−0.09188 (9)	−0.05555 (11)	0.0147 (3)
C5B	0.55395 (9)	−0.03839 (9)	−0.06403 (12)	0.0154 (3)
H5B	0.5486	0.0171	−0.0738	0.018*
C1B	0.69976 (9)	−0.04680 (10)	−0.05951 (12)	0.0154 (3)
O1B	0.70693 (7)	0.02492 (7)	−0.06251 (9)	0.0200 (2)
C2B	0.76622 (10)	−0.10523 (10)	−0.05829 (13)	0.0194 (3)
H2B1	0.7607	−0.1415	−0.1152	0.029*
H2B2	0.7647	−0.1354	0.0045	0.029*
H2B3	0.8168	−0.0771	−0.0634	0.029*
C6B	0.40835 (10)	−0.07816 (9)	−0.05750 (11)	0.0154 (3)
O6B	0.35887 (7)	−0.13051 (7)	−0.05231 (10)	0.0225 (3)
O7B	0.39068 (7)	−0.00061 (7)	−0.06476 (9)	0.0191 (2)
C7B	0.30717 (10)	0.02022 (10)	−0.05846 (14)	0.0210 (3)
H7B1	0.2818	−0.0080	−0.0019	0.025*
H7B2	0.2795	0.0055	−0.1212	0.025*
C8B	0.30300 (11)	0.10842 (11)	−0.04233 (14)	0.0244 (4)
H8B1	0.2475	0.1248	−0.0369	0.037*
H8B2	0.3278	0.1356	−0.0992	0.037*
H8B3	0.3310	0.1223	0.0196	0.037*
N1C	0.01782 (8)	−0.00079 (9)	−0.05932 (11)	0.0165 (3)
N2C	−0.06377 (8)	0.01086 (8)	−0.05705 (11)	0.0170 (3)
C3C	−0.07160 (10)	0.08937 (10)	−0.05517 (12)	0.0164 (3)
N3C	−0.14403 (9)	0.12397 (9)	−0.05203 (14)	0.0260 (3)
H3C1	−0.1870	0.0945	−0.0512	0.031*
H3C2	−0.1481	0.1759	−0.0508	0.031*
C4C	0.00407 (10)	0.12862 (10)	−0.05552 (12)	0.0157 (3)
C5C	0.05886 (10)	0.06857 (10)	−0.05807 (13)	0.0166 (3)
H5C	0.1148	0.0743	−0.0588	0.020*
C1C	0.05042 (10)	−0.07720 (10)	−0.06280 (13)	0.0178 (3)
O1C	0.12252 (7)	−0.08368 (7)	−0.06662 (11)	0.0245 (3)
C2C	−0.00724 (10)	−0.14406 (10)	−0.06131 (14)	0.0208 (3)
H2C1	−0.0426	−0.1399	−0.1193	0.031*
H2C2	−0.0385	−0.1418	0.0006	0.031*
H2C3	0.0215	−0.1944	−0.0642	0.031*
C6C	0.01798 (10)	0.21369 (10)	−0.05072 (11)	0.0159 (3)
O6C	−0.03495 (8)	0.26289 (7)	−0.04565 (10)	0.0220 (3)
O7C	0.09531 (7)	0.23157 (7)	−0.05256 (10)	0.0194 (2)
C7C	0.11517 (10)	0.31519 (10)	−0.04406 (13)	0.0201 (3)
H7C1	0.0948	0.3372	0.0198	0.024*
H7C2	0.0919	0.3455	−0.1004	0.024*
C8C	0.20495 (11)	0.31965 (11)	−0.04708 (16)	0.0273 (4)
H8C1	0.2217	0.3749	−0.0396	0.041*
H8C2	0.2240	0.2990	−0.1114	0.041*
H8C3	0.2270	0.2880	0.0078	0.041*
N1D	0.09337 (8)	0.60341 (8)	−0.05500 (10)	0.0153 (2)
N2D	0.10333 (8)	0.68533 (8)	−0.05801 (11)	0.0164 (3)
C3D	0.18154 (10)	0.69497 (9)	−0.05153 (11)	0.0147 (3)
N3D	0.21495 (9)	0.76747 (9)	−0.05148 (13)	0.0230 (3)
H3D1	0.1850	0.8100	−0.0558	0.028*
H3D2	0.2667	0.7723	−0.0471	0.028*
C4D	0.22180 (10)	0.61992 (10)	−0.04407 (11)	0.0146 (3)
C5D	0.16309 (10)	0.56408 (10)	−0.04728 (12)	0.0152 (3)
H5D	0.1699	0.5083	−0.0446	0.018*
C1D	0.01774 (9)	0.56863 (10)	−0.05765 (12)	0.0166 (3)
O1D	0.01262 (8)	0.49680 (8)	−0.05167 (10)	0.0245 (3)
C2D	−0.05075 (10)	0.62425 (11)	−0.06884 (13)	0.0204 (3)
H2D1	−0.0467	0.6664	−0.0185	0.031*
H2D3	−0.1004	0.5952	−0.0592	0.031*
H2D2	−0.0500	0.6476	−0.1361	0.031*
C6D	0.30720 (10)	0.60728 (10)	−0.03765 (11)	0.0150 (3)
O6D	0.35621 (7)	0.65981 (7)	−0.03678 (10)	0.0216 (3)
O7D	0.32498 (7)	0.52980 (7)	−0.03240 (9)	0.0173 (2)
C7D	0.40862 (10)	0.50955 (10)	−0.03342 (13)	0.0189 (3)
H7D1	0.4366	0.5361	0.0224	0.023*
H7D2	0.4333	0.5261	−0.0975	0.023*
C8D	0.41276 (12)	0.42080 (11)	−0.02165 (16)	0.0271 (4)
H8D1	0.4681	0.4036	−0.0254	0.041*
H8D2	0.3824	0.3955	−0.0754	0.041*
H8D3	0.3905	0.4057	0.0435	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0118 (7)	0.0121 (7)	0.0203 (5)	0.0002 (5)	0.0006 (5)	0.0012 (5)
N2A	0.0112 (7)	0.0148 (7)	0.0204 (6)	0.0003 (5)	0.0008 (5)	0.0008 (5)
C3A	0.0138 (8)	0.0158 (8)	0.0160 (6)	0.0015 (6)	0.0000 (5)	0.0000 (5)
N3A	0.0137 (7)	0.0138 (7)	0.0308 (7)	0.0018 (5)	0.0033 (5)	−0.0015 (6)
C4A	0.0135 (8)	0.0130 (8)	0.0178 (6)	−0.0019 (6)	−0.0007 (5)	0.0001 (5)
C5A	0.0125 (8)	0.0143 (8)	0.0204 (6)	−0.0020 (6)	0.0002 (6)	0.0008 (6)
C1A	0.0168 (8)	0.0138 (8)	0.0180 (6)	0.0020 (6)	0.0005 (6)	0.0006 (5)
O1A	0.0165 (6)	0.0188 (7)	0.0324 (6)	0.0025 (5)	0.0008 (5)	0.0010 (5)
C2A	0.0195 (9)	0.0132 (8)	0.0272 (7)	−0.0002 (6)	0.0028 (6)	0.0002 (6)
C6A	0.0149 (8)	0.0143 (8)	0.0189 (6)	−0.0024 (6)	−0.0006 (6)	0.0001 (5)
O6A	0.0191 (7)	0.0153 (6)	0.0385 (7)	0.0042 (5)	−0.0002 (5)	−0.0003 (5)
O7A	0.0158 (6)	0.0126 (6)	0.0291 (6)	−0.0026 (4)	−0.0005 (5)	−0.0002 (5)
C7A	0.0238 (9)	0.0091 (8)	0.0293 (8)	−0.0047 (6)	−0.0023 (7)	0.0001 (6)
C8A	0.0251 (10)	0.0232 (10)	0.0284 (8)	−0.0065 (8)	−0.0041 (7)	−0.0006 (7)
N1B	0.0131 (6)	0.0106 (6)	0.0201 (5)	−0.0003 (5)	0.0004 (5)	0.0002 (5)
N2B	0.0145 (7)	0.0115 (6)	0.0214 (6)	−0.0019 (5)	−0.0008 (5)	0.0021 (5)
C3B	0.0151 (8)	0.0148 (8)	0.0160 (6)	−0.0014 (6)	0.0003 (5)	0.0014 (5)
N3B	0.0151 (7)	0.0144 (7)	0.0333 (7)	−0.0019 (6)	−0.0019 (6)	0.0044 (6)
C4B	0.0135 (8)	0.0138 (8)	0.0167 (6)	−0.0001 (5)	−0.0005 (5)	−0.0002 (5)
C5B	0.0149 (8)	0.0132 (7)	0.0180 (6)	0.0015 (6)	−0.0002 (6)	0.0004 (5)
C1B	0.0122 (7)	0.0162 (8)	0.0179 (6)	−0.0022 (6)	0.0004 (5)	−0.0001 (6)
O1B	0.0167 (6)	0.0147 (6)	0.0286 (6)	−0.0033 (5)	0.0003 (5)	0.0007 (5)
C2B	0.0128 (8)	0.0182 (8)	0.0271 (7)	0.0002 (6)	0.0019 (6)	0.0009 (6)
C6B	0.0146 (8)	0.0152 (8)	0.0165 (6)	0.0012 (6)	−0.0003 (6)	0.0004 (6)
O6B	0.0150 (6)	0.0182 (6)	0.0344 (6)	−0.0041 (5)	0.0007 (5)	−0.0007 (5)
O7B	0.0128 (6)	0.0154 (6)	0.0291 (6)	0.0020 (4)	−0.0004 (5)	0.0018 (5)
C7B	0.0122 (8)	0.0224 (9)	0.0283 (7)	0.0042 (6)	−0.0001 (6)	−0.0012 (7)
C8B	0.0210 (10)	0.0227 (10)	0.0296 (8)	0.0050 (7)	−0.0020 (7)	−0.0019 (7)
N1C	0.0107 (7)	0.0146 (6)	0.0242 (6)	0.0007 (5)	0.0001 (5)	0.0008 (5)
N2C	0.0105 (6)	0.0148 (7)	0.0255 (6)	0.0021 (5)	0.0008 (5)	0.0003 (5)
C3C	0.0147 (8)	0.0149 (8)	0.0195 (6)	0.0005 (6)	−0.0012 (6)	0.0001 (6)
N3C	0.0149 (8)	0.0158 (7)	0.0473 (9)	0.0018 (6)	−0.0011 (7)	−0.0028 (7)
C4C	0.0139 (8)	0.0160 (8)	0.0172 (6)	−0.0017 (6)	−0.0008 (6)	−0.0009 (6)
C5C	0.0136 (8)	0.0149 (8)	0.0212 (6)	−0.0021 (6)	−0.0002 (6)	0.0000 (6)
C1C	0.0168 (8)	0.0144 (8)	0.0220 (7)	0.0022 (6)	0.0012 (6)	0.0006 (6)
O1C	0.0159 (6)	0.0188 (6)	0.0387 (7)	0.0045 (5)	0.0021 (5)	0.0004 (5)
C2C	0.0178 (8)	0.0139 (8)	0.0307 (8)	0.0022 (6)	0.0033 (7)	−0.0001 (7)
C6C	0.0147 (8)	0.0155 (8)	0.0176 (6)	−0.0021 (6)	0.0002 (5)	0.0004 (5)
O6C	0.0200 (6)	0.0135 (6)	0.0325 (6)	0.0026 (5)	−0.0013 (5)	−0.0012 (5)
O7C	0.0156 (6)	0.0128 (6)	0.0299 (6)	−0.0023 (4)	0.0007 (5)	−0.0012 (5)
C7C	0.0211 (9)	0.0124 (8)	0.0269 (8)	−0.0048 (6)	0.0009 (6)	−0.0003 (6)
C8C	0.0225 (10)	0.0221 (10)	0.0373 (10)	−0.0082 (7)	0.0049 (8)	−0.0052 (8)
N1D	0.0131 (7)	0.0133 (6)	0.0196 (6)	−0.0012 (5)	0.0002 (5)	0.0022 (5)
N2D	0.0153 (7)	0.0124 (7)	0.0216 (6)	−0.0012 (5)	−0.0001 (5)	0.0013 (5)
C3D	0.0135 (8)	0.0146 (8)	0.0160 (6)	−0.0007 (6)	0.0002 (5)	0.0002 (5)
N3D	0.0143 (7)	0.0122 (7)	0.0425 (9)	−0.0010 (5)	0.0012 (6)	−0.0022 (6)
C4D	0.0125 (8)	0.0149 (8)	0.0164 (6)	0.0014 (6)	0.0000 (5)	0.0003 (5)
C5D	0.0122 (8)	0.0142 (8)	0.0191 (6)	0.0011 (6)	−0.0011 (5)	0.0014 (5)
C1D	0.0124 (7)	0.0190 (8)	0.0185 (6)	−0.0021 (6)	0.0001 (6)	0.0024 (6)
O1D	0.0201 (7)	0.0177 (6)	0.0357 (7)	−0.0045 (5)	0.0022 (6)	0.0024 (5)
C2D	0.0129 (8)	0.0211 (9)	0.0273 (8)	−0.0003 (6)	−0.0004 (6)	0.0035 (6)
C6D	0.0132 (8)	0.0150 (8)	0.0167 (6)	0.0014 (6)	−0.0008 (5)	−0.0006 (5)
O6D	0.0158 (6)	0.0166 (6)	0.0324 (6)	−0.0018 (5)	−0.0019 (5)	−0.0009 (5)
O7D	0.0116 (6)	0.0151 (6)	0.0253 (5)	0.0028 (4)	−0.0011 (4)	0.0005 (4)
C7D	0.0109 (8)	0.0214 (9)	0.0243 (7)	0.0043 (6)	−0.0016 (6)	−0.0016 (6)
C8D	0.0214 (10)	0.0223 (10)	0.0377 (9)	0.0068 (7)	0.0032 (8)	0.0079 (8)

Geometric parameters (Å, º) top

N1A—C5A	1.353 (2)	N1C—C5C	1.361 (2)
N1A—N2A	1.391 (2)	N1C—N2C	1.392 (2)
N1A—C1A	1.411 (2)	N1C—C1C	1.404 (2)
N2A—C3A	1.333 (2)	N2C—C3C	1.332 (2)
C3A—N3A	1.346 (2)	C3C—N3C	1.356 (2)
C3A—C4A	1.441 (2)	C3C—C4C	1.440 (2)
N3A—H3A1	0.88	N3C—H3C1	0.8800
N3A—H3A2	0.88	N3C—H3C2	0.8800
C4A—C5A	1.377 (2)	C4C—C5C	1.373 (2)
C4A—C6A	1.457 (2)	C4C—C6C	1.457 (2)
C5A—H5A	0.95	C5C—H5C	0.9500
C1A—O1A	1.223 (2)	C1C—O1C	1.224 (2)
C1A—C2A	1.484 (2)	C1C—C2C	1.491 (2)
C2A—H2A1	0.98	C2C—H2C1	0.9800
C2A—H2A2	0.98	C2C—H2C2	0.9800
C2A—H2A3	0.98	C2C—H2C3	0.9800
C6A—O6A	1.214 (2)	C6C—O6C	1.222 (2)
C6A—O7A	1.351 (2)	C6C—O7C	1.341 (2)
O7A—C7A	1.459 (2)	O7C—C7C	1.456 (2)
C7A—C8A	1.511 (3)	C7C—C8C	1.518 (3)
C7A—H7A1	0.9900	C7C—H7C1	0.9900
C7A—H7A2	0.9900	C7C—H7C2	0.9900
C8A—H8A1	0.9800	C8C—H8C1	0.9800
C8A—H8A2	0.9800	C8C—H8C2	0.9800
C8A—H8A3	0.9800	C8C—H8C3	0.9800
N1B—C5B	1.363 (2)	N1D—C5D	1.356 (2)
N1B—N2B	1.390 (2)	N1D—N2D	1.394 (2)
N1B—C1B	1.404 (2)	N1D—C1D	1.406 (2)
N2B—C3B	1.335 (2)	N2D—C3D	1.333 (2)
C3B—N3B	1.352 (2)	C3D—N3D	1.348 (2)
C3B—C4B	1.446 (2)	C3D—C4D	1.442 (2)
N3B—H3B1	0.8800	N3D—H3D1	0.8800
N3B—H3B2	0.8800	N3D—H3D2	0.8800
C4B—C5B	1.365 (2)	C4D—C5D	1.369 (2)
C4B—C6B	1.460 (2)	C4D—C6D	1.460 (2)
C5B—H5B	0.9500	C5D—H5D	0.9500
C1B—O1B	1.218 (2)	C1D—O1D	1.219 (2)
C1B—C2B	1.494 (2)	C1D—C2D	1.497 (2)
C2B—H2B1	0.9800	C2D—H2D1	0.9800
C2B—H2B2	0.9800	C2D—H2D3	0.9800
C2B—H2B3	0.9800	C2D—H2D2	0.9800
C6B—O6B	1.219 (2)	C6D—O6D	1.213 (2)
C6B—O7B	1.347 (2)	C6D—O7D	1.344 (2)
O7B—C7B	1.456 (2)	O7D—C7D	1.453 (2)
C7B—C8B	1.507 (2)	C7D—C8D	1.508 (2)
C7B—H7B1	0.9900	C7D—H7D1	0.9900
C7B—H7B2	0.9900	C7D—H7D2	0.9900
C8B—H8B1	0.9800	C8D—H8D1	0.9800
C8B—H8B2	0.9800	C8D—H8D2	0.9800
C8B—H8B3	0.9800	C8D—H8D3	0.9800

C5A—N1A—N2A	112.66 (13)	C5C—N1C—N2C	112.45 (13)
C5A—N1A—C1A	125.80 (14)	C5C—N1C—C1C	126.29 (14)
N2A—N1A—C1A	121.52 (13)	N2C—N1C—C1C	121.26 (13)
C3A—N2A—N1A	104.19 (13)	C3C—N2C—N1C	103.85 (13)
N2A—C3A—N3A	122.13 (16)	N2C—C3C—N3C	121.25 (15)
N2A—C3A—C4A	111.10 (14)	N2C—C3C—C4C	111.71 (14)
N3A—C3A—C4A	126.73 (16)	N3C—C3C—C4C	127.04 (16)
C3A—N3A—H3A1	120.0	C3C—N3C—H3C1	120.0
C3A—N3A—H3A2	120.0	C3C—N3C—H3C2	120.0
H3A1—N3A—H3A2	120.0	H3C1—N3C—H3C2	120.0
C5A—C4A—C3A	105.17 (14)	C5C—C4C—C3C	104.96 (14)
C5A—C4A—C6A	128.04 (15)	C5C—C4C—C6C	128.36 (15)
C3A—C4A—C6A	126.76 (15)	C3C—C4C—C6C	126.65 (15)
N1A—C5A—C4A	106.88 (14)	N1C—C5C—C4C	107.03 (14)
N1A—C5A—H5A	126.6	N1C—C5C—H5C	126.5
C4A—C5A—H5A	126.6	C4C—C5C—H5C	126.5
O1A—C1A—N1A	118.11 (15)	O1C—C1C—N1C	118.29 (15)
O1A—C1A—C2A	125.92 (15)	O1C—C1C—C2C	125.63 (15)
N1A—C1A—C2A	115.97 (14)	N1C—C1C—C2C	116.08 (14)
C1A—C2A—H2A1	109.5	C1C—C2C—H2C1	109.5
C1A—C2A—H2A2	109.5	C1C—C2C—H2C2	109.5
H2A1—C2A—H2A2	109.5	H2C1—C2C—H2C2	109.5
C1A—C2A—H2A3	109.5	C1C—C2C—H2C3	109.5
H2A1—C2A—H2A3	109.5	H2C1—C2C—H2C3	109.5
H2A2—C2A—H2A3	109.5	H2C2—C2C—H2C3	109.5
O6A—C6A—O7A	123.64 (15)	O6C—C6C—O7C	124.08 (15)
O6A—C6A—C4A	124.69 (15)	O6C—C6C—C4C	123.69 (15)
O7A—C6A—C4A	111.67 (14)	O7C—C6C—C4C	112.23 (14)
C6A—O7A—C7A	116.32 (13)	C6C—O7C—C7C	116.20 (13)
O7A—C7A—C8A	106.63 (15)	O7C—C7C—C8C	106.02 (14)
O7A—C7A—H7A1	110.4	O7C—C7C—H7C1	110.5
C8A—C7A—H7A1	110.4	C8C—C7C—H7C1	110.5
O7A—C7A—H7A2	110.4	O7C—C7C—H7C2	110.5
C8A—C7A—H7A2	110.4	C8C—C7C—H7C2	110.5
H7A1—C7A—H7A2	108.6	H7C1—C7C—H7C2	108.7
C7A—C8A—H8A1	109.5	C7C—C8C—H8C1	109.5
C7A—C8A—H8A2	109.5	C7C—C8C—H8C2	109.5
H8A1—C8A—H8A2	109.5	H8C1—C8C—H8C2	109.5
C7A—C8A—H8A3	109.5	C7C—C8C—H8C3	109.5
H8A1—C8A—H8A3	109.5	H8C1—C8C—H8C3	109.5
H8A2—C8A—H8A3	109.5	H8C2—C8C—H8C3	109.5
C5B—N1B—N2B	112.38 (13)	C5D—N1D—N2D	112.55 (13)
C5B—N1B—C1B	126.16 (14)	C5D—N1D—C1D	125.88 (14)
N2B—N1B—C1B	121.46 (13)	N2D—N1D—C1D	121.55 (13)
C3B—N2B—N1B	103.88 (13)	C3D—N2D—N1D	103.81 (13)
N2B—C3B—N3B	121.78 (15)	N2D—C3D—N3D	121.69 (15)
N2B—C3B—C4B	111.50 (14)	N2D—C3D—C4D	111.36 (14)
N3B—C3B—C4B	126.67 (15)	N3D—C3D—C4D	126.94 (15)
C3B—N3B—H3B1	120.0	C3D—N3D—H3D1	120.0
C3B—N3B—H3B2	120.0	C3D—N3D—H3D2	120.0
H3B1—N3B—H3B2	120.0	H3D1—N3D—H3D2	120.0
C5B—C4B—C3B	104.87 (14)	C5D—C4D—C3D	105.18 (14)
C5B—C4B—C6B	129.00 (15)	C5D—C4D—C6D	128.05 (15)
C3B—C4B—C6B	126.12 (14)	C3D—C4D—C6D	126.75 (15)
N1B—C5B—C4B	107.37 (14)	N1D—C5D—C4D	107.09 (14)
N1B—C5B—H5B	126.3	N1D—C5D—H5D	126.5
C4B—C5B—H5B	126.3	C4D—C5D—H5D	126.5
O1B—C1B—N1B	118.72 (15)	O1D—C1D—N1D	118.58 (15)
O1B—C1B—C2B	125.61 (15)	O1D—C1D—C2D	125.17 (15)
N1B—C1B—C2B	115.67 (14)	N1D—C1D—C2D	116.24 (14)
C1B—C2B—H2B1	109.5	C1D—C2D—H2D1	109.5
C1B—C2B—H2B2	109.5	C1D—C2D—H2D3	109.5
H2B1—C2B—H2B2	109.5	H2D1—C2D—H2D3	109.5
C1B—C2B—H2B3	109.5	C1D—C2D—H2D2	109.5
H2B1—C2B—H2B3	109.5	H2D1—C2D—H2D2	109.5
H2B2—C2B—H2B3	109.5	H2D3—C2D—H2D2	109.5
O6B—C6B—O7B	123.90 (15)	O6D—C6D—O7D	123.96 (15)
O6B—C6B—C4B	124.12 (15)	O6D—C6D—C4D	124.57 (15)
O7B—C6B—C4B	111.98 (14)	O7D—C6D—C4D	111.47 (14)
C6B—O7B—C7B	116.45 (13)	C6D—O7D—C7D	116.47 (13)
O7B—C7B—C8B	107.00 (14)	O7D—C7D—C8D	106.13 (14)
O7B—C7B—H7B1	110.3	O7D—C7D—H7D1	110.5
C8B—C7B—H7B1	110.3	C8D—C7D—H7D1	110.5
O7B—C7B—H7B2	110.3	O7D—C7D—H7D2	110.5
C8B—C7B—H7B2	110.3	C8D—C7D—H7D2	110.5
H7B1—C7B—H7B2	108.6	H7D1—C7D—H7D2	108.7
C7B—C8B—H8B1	109.5	C7D—C8D—H8D1	109.5
C7B—C8B—H8B2	109.5	C7D—C8D—H8D2	109.5
H8B1—C8B—H8B2	109.5	H8D1—C8D—H8D2	109.5
C7B—C8B—H8B3	109.5	C7D—C8D—H8D3	109.5
H8B1—C8B—H8B3	109.5	H8D1—C8D—H8D3	109.5
H8B2—C8B—H8B3	109.5	H8D2—C8D—H8D3	109.5

C5A—N1A—N2A—C3A	0.28 (17)	C5C—N1C—N2C—C3C	0.47 (19)
C1A—N1A—N2A—C3A	−178.30 (13)	C1C—N1C—N2C—C3C	−179.34 (14)
N1A—N2A—C3A—N3A	177.63 (15)	N1C—N2C—C3C—N3C	−179.60 (16)
N1A—N2A—C3A—C4A	−0.38 (16)	N1C—N2C—C3C—C4C	−0.39 (18)
N2A—C3A—C4A—C5A	0.35 (18)	N2C—C3C—C4C—C5C	0.19 (19)
N3A—C3A—C4A—C5A	−177.54 (16)	N3C—C3C—C4C—C5C	179.34 (18)
N2A—C3A—C4A—C6A	178.40 (15)	N2C—C3C—C4C—C6C	−177.95 (15)
N3A—C3A—C4A—C6A	0.5 (3)	N3C—C3C—C4C—C6C	1.2 (3)
N2A—N1A—C5A—C4A	−0.07 (18)	N2C—N1C—C5C—C4C	−0.36 (19)
C1A—N1A—C5A—C4A	178.45 (14)	C1C—N1C—C5C—C4C	179.43 (15)
C3A—C4A—C5A—N1A	−0.16 (17)	C3C—C4C—C5C—N1C	0.11 (17)
C6A—C4A—C5A—N1A	−178.17 (15)	C6C—C4C—C5C—N1C	178.21 (15)
C5A—N1A—C1A—O1A	−3.1 (2)	C5C—N1C—C1C—O1C	−1.2 (2)
N2A—N1A—C1A—O1A	175.31 (14)	N2C—N1C—C1C—O1C	178.62 (15)
C5A—N1A—C1A—C2A	176.31 (15)	C5C—N1C—C1C—C2C	178.74 (16)
N2A—N1A—C1A—C2A	−5.3 (2)	N2C—N1C—C1C—C2C	−1.5 (2)
C5A—C4A—C6A—O6A	−177.91 (17)	C5C—C4C—C6C—O6C	−177.69 (17)
C3A—C4A—C6A—O6A	4.5 (3)	C3C—C4C—C6C—O6C	0.0 (3)
C5A—C4A—C6A—O7A	2.4 (2)	C5C—C4C—C6C—O7C	2.3 (2)
C3A—C4A—C6A—O7A	−175.19 (14)	C3C—C4C—C6C—O7C	−179.94 (14)
O6A—C6A—O7A—C7A	−2.3 (2)	O6C—C6C—O7C—C7C	2.4 (2)
C4A—C6A—O7A—C7A	177.41 (13)	C4C—C6C—O7C—C7C	−177.66 (13)
C6A—O7A—C7A—C8A	−169.86 (14)	C6C—O7C—C7C—C8C	179.49 (14)
C5B—N1B—N2B—C3B	−0.61 (17)	C5D—N1D—N2D—C3D	−0.20 (17)
C1B—N1B—N2B—C3B	179.09 (13)	C1D—N1D—N2D—C3D	178.47 (13)
N1B—N2B—C3B—N3B	−176.95 (14)	N1D—N2D—C3D—N3D	−179.65 (15)
N1B—N2B—C3B—C4B	0.63 (16)	N1D—N2D—C3D—C4D	−0.19 (17)
N2B—C3B—C4B—C5B	−0.45 (17)	N2D—C3D—C4D—C5D	0.49 (18)
N3B—C3B—C4B—C5B	176.99 (16)	N3D—C3D—C4D—C5D	179.92 (16)
N2B—C3B—C4B—C6B	−179.34 (14)	N2D—C3D—C4D—C6D	178.79 (14)
N3B—C3B—C4B—C6B	−1.9 (3)	N3D—C3D—C4D—C6D	−1.8 (3)
N2B—N1B—C5B—C4B	0.34 (18)	N2D—N1D—C5D—C4D	0.52 (18)
C1B—N1B—C5B—C4B	−179.34 (14)	C1D—N1D—C5D—C4D	−178.09 (14)
C3B—C4B—C5B—N1B	0.05 (17)	C3D—C4D—C5D—N1D	−0.58 (17)
C6B—C4B—C5B—N1B	178.90 (15)	C6D—C4D—C5D—N1D	−178.85 (14)
C5B—N1B—C1B—O1B	6.0 (2)	C5D—N1D—C1D—O1D	0.7 (2)
N2B—N1B—C1B—O1B	−173.65 (14)	N2D—N1D—C1D—O1D	−177.76 (14)
C5B—N1B—C1B—C2B	−174.56 (15)	C5D—N1D—C1D—C2D	−178.67 (15)
N2B—N1B—C1B—C2B	5.8 (2)	N2D—N1D—C1D—C2D	2.8 (2)
C5B—C4B—C6B—O6B	177.68 (16)	C5D—C4D—C6D—O6D	178.70 (16)
C3B—C4B—C6B—O6B	−3.7 (3)	C3D—C4D—C6D—O6D	0.8 (2)
C5B—C4B—C6B—O7B	−2.9 (2)	C5D—C4D—C6D—O7D	−1.5 (2)
C3B—C4B—C6B—O7B	175.70 (14)	C3D—C4D—C6D—O7D	−179.46 (14)
O6B—C6B—O7B—C7B	4.6 (2)	O6D—C6D—O7D—C7D	−4.8 (2)
C4B—C6B—O7B—C7B	−174.80 (13)	C4D—C6D—O7D—C7D	175.47 (13)
C6B—O7B—C7B—C8B	166.16 (13)	C6D—O7D—C7D—C8D	177.23 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A2···O6A	0.88	2.43	3.003 (2)	124
N3A—H3A2···O6Cⁱ	0.88	2.26	2.948 (2)	135
N3A—H3A1···O1Dⁱ	0.88	2.14	3.015 (2)	173
N3B—H3B2···O6B	0.88	2.40	2.977 (2)	124
N3B—H3B2···O6Dⁱⁱ	0.88	2.25	2.941 (2)	136
N3B—H3B1···O1Aⁱⁱ	0.88	2.18	3.050 (2)	171
N3C—H3C2···O6C	0.88	2.41	2.984 (2)	123
N3C—H3C2···O6Aⁱⁱⁱ	0.88	2.27	2.964 (2)	135
N3C—H3C1···O1Bⁱⁱⁱ	0.88	2.15	3.025 (2)	175
N3D—H3D2···O6D	0.88	2.43	3.006 (2)	123
N3D—H3D1···O1C^iv	0.88	2.09	2.966 (2)	175
N3D—H3D2···O6B^iv	0.88	2.26	2.979 (2)	139

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

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Ethyl 1-acetyl-3-amino-1H-pyrazole-4-carboxyl­ate, a tetra­gonal structure with Z′ = 4

Supporting information

Key indicators

checkCIF/PLATON results

Ethyl 1-acetyl-3-amino-1H-pyrazole-4-carboxylate, a tetragonal structure with Z′ = 4