Di­methyl 1-(7-acetoxy-4-methyl-2-oxo-2H-chromen-8-yl­methyl)-1H-pyrazole-3,4-di­carboxyl­ate

In the title compound, C₂₀H₁₈N₂O₈, the coumarin moiety is oriented approximately perpendicular to the plane of the pyrazole ring. Weak intermolecular C—H...O interactions link the mol­ecules into a complex network that can be represented by C(X) chains (X is 8, 10, 11 and 13) and R₂²(26) and R₂²(10) rings.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.148
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.28
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C25

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Dimethyl 1-(7-acetoxy-4-methyl-2-oxo-2H-chromen-8-ylmethyl)-1H-pyrazole- 3,4-dicarboxylate

Crystal data

C20H18N2O8	F(000) = 1728
Mr = 414.36	Dx = 1.365 Mg m^−3
Monoclinic, C2/c	Melting point: 458 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 23.1233 (17) Å	Cell parameters from 3600 reflections
b = 12.7597 (9) Å	θ = 2.5–26.0°
c = 15.2076 (11) Å	µ = 0.11 mm^−1
β = 116.032 (1)°	T = 273 K
V = 4031.7 (5) Å^3	Prism, colourless
Z = 8	0.25 × 0.18 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3177 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 28.0°, θmin = 1.9°
ω scans	h = −30→30
12054 measured reflections	k = −15→16
4672 independent reflections	l = −17→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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0801P)^2 + 0.4379P] where P = (Fo^2 + 2Fc^2)/3
4672 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.13 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
O7	0.41253 (5)	0.48413 (9)	1.11549 (8)	0.0628 (3)
O8	0.38625 (8)	0.31827 (12)	1.10905 (11)	0.0961 (5)
O17	0.21833 (7)	0.85615 (12)	0.75430 (11)	0.0935 (5)
O18	0.24750 (7)	0.71362 (13)	0.69901 (9)	0.0942 (5)
O20	0.14762 (6)	0.58903 (11)	0.72357 (10)	0.0897 (4)
O21	0.17608 (7)	0.46325 (11)	0.83619 (9)	0.0845 (4)
O24	0.45171 (6)	0.84529 (10)	1.11017 (9)	0.0740 (4)
O25	0.45636 (8)	0.86242 (13)	0.96651 (11)	0.1013 (5)
N1	0.31646 (5)	0.67234 (11)	1.00794 (9)	0.0552 (3)
N2	0.30937 (6)	0.74628 (11)	0.94023 (9)	0.0590 (3)
C3	0.26211 (7)	0.70962 (13)	0.85881 (11)	0.0553 (4)
C4	0.23865 (7)	0.61353 (13)	0.87367 (11)	0.0562 (4)
C5	0.27553 (7)	0.59314 (13)	0.97156 (12)	0.0577 (4)
H5	0.2724	0.5348	1.0058	0.069*
C6	0.36691 (7)	0.68521 (14)	1.10797 (11)	0.0604 (4)
H61	0.3586	0.6380	1.1511	0.072*
H62	0.3656	0.7563	1.1296	0.072*
C8	0.42772 (10)	0.37891 (16)	1.11713 (12)	0.0711 (5)
C9	0.49138 (10)	0.35540 (16)	1.12814 (12)	0.0759 (5)
H9	0.5029	0.2854	1.1294	0.091*
C10	0.53472 (8)	0.42806 (16)	1.13657 (11)	0.0672 (5)
C11	0.55697 (7)	0.62142 (16)	1.13807 (11)	0.0654 (5)
H11	0.5987	0.6083	1.1469	0.078*
C12	0.53632 (8)	0.72242 (16)	1.13097 (12)	0.0674 (5)
H12	0.5637	0.7774	1.1348	0.081*
C13	0.47422 (7)	0.74265 (14)	1.11806 (11)	0.0605 (4)
C14	0.43299 (7)	0.66326 (13)	1.11562 (10)	0.0537 (4)
C15	0.45535 (7)	0.56165 (13)	1.12190 (10)	0.0531 (4)
C16	0.51701 (7)	0.53736 (14)	1.13239 (9)	0.0565 (4)
C17	0.24019 (8)	0.77012 (16)	0.76611 (13)	0.0669 (5)
C19	0.21950 (15)	0.7546 (2)	0.60026 (16)	0.1256 (10)
H191	0.1734	0.7531	0.5741	0.188*
H192	0.2329	0.7123	0.5602	0.188*
H193	0.2336	0.8254	0.6010	0.188*
C20	0.18339 (8)	0.55592 (14)	0.80234 (13)	0.0653 (4)
C22	0.12247 (13)	0.4017 (2)	0.76876 (19)	0.1168 (9)
H221	0.0831	0.4392	0.7526	0.175*
H222	0.1212	0.3360	0.7986	0.175*
H223	0.1275	0.3892	0.7102	0.175*
C23	0.60081 (10)	0.3985 (2)	1.15019 (16)	0.0951 (7)
H231	0.6314	0.4134	1.2162	0.143*
H232	0.6115	0.4382	1.1057	0.143*
H233	0.6019	0.3251	1.1373	0.143*
C25	0.44185 (10)	0.89844 (17)	1.02590 (16)	0.0821 (6)
C26	0.41081 (16)	1.00115 (19)	1.0214 (2)	0.1205 (9)
H261	0.4039	1.0363	0.9618	0.181*
H262	0.4382	1.0432	1.0763	0.181*
H263	0.3702	0.9905	1.0232	0.181*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0544 (6)	0.0754 (8)	0.0540 (6)	−0.0009 (5)	0.0196 (5)	0.0035 (5)
O8	0.1002 (10)	0.0873 (10)	0.0869 (10)	−0.0199 (8)	0.0282 (8)	0.0036 (8)
O17	0.0940 (10)	0.0962 (11)	0.0894 (10)	0.0260 (8)	0.0393 (8)	0.0348 (8)
O18	0.1101 (11)	0.1200 (12)	0.0571 (8)	0.0167 (9)	0.0409 (8)	0.0142 (8)
O20	0.0818 (8)	0.0853 (9)	0.0687 (8)	0.0042 (7)	0.0024 (7)	0.0048 (7)
O21	0.0935 (9)	0.0760 (9)	0.0696 (8)	−0.0120 (7)	0.0226 (7)	0.0001 (7)
O24	0.0877 (8)	0.0731 (8)	0.0648 (8)	0.0009 (6)	0.0367 (6)	−0.0029 (6)
O25	0.1260 (12)	0.1144 (13)	0.0775 (9)	0.0229 (10)	0.0576 (9)	0.0178 (8)
N1	0.0457 (6)	0.0710 (8)	0.0492 (7)	0.0101 (6)	0.0211 (5)	0.0060 (6)
N2	0.0494 (7)	0.0735 (9)	0.0554 (8)	0.0086 (6)	0.0243 (6)	0.0072 (6)
C3	0.0462 (7)	0.0705 (10)	0.0513 (8)	0.0143 (7)	0.0232 (7)	0.0065 (7)
C4	0.0502 (7)	0.0655 (10)	0.0526 (9)	0.0116 (7)	0.0222 (7)	0.0014 (7)
C5	0.0532 (8)	0.0644 (10)	0.0578 (9)	0.0100 (7)	0.0263 (7)	0.0077 (7)
C6	0.0533 (8)	0.0820 (12)	0.0460 (8)	0.0088 (7)	0.0219 (7)	−0.0011 (7)
C8	0.0802 (12)	0.0753 (12)	0.0467 (9)	−0.0033 (10)	0.0178 (8)	0.0029 (8)
C9	0.0895 (13)	0.0766 (13)	0.0551 (10)	0.0188 (10)	0.0257 (9)	0.0043 (9)
C10	0.0670 (10)	0.0927 (13)	0.0384 (8)	0.0218 (9)	0.0199 (7)	0.0046 (8)
C11	0.0437 (7)	0.1050 (14)	0.0442 (8)	0.0031 (8)	0.0162 (6)	−0.0003 (8)
C12	0.0554 (9)	0.0910 (13)	0.0518 (9)	−0.0138 (9)	0.0200 (7)	−0.0044 (8)
C13	0.0611 (9)	0.0748 (11)	0.0422 (8)	0.0003 (8)	0.0194 (7)	−0.0022 (7)
C14	0.0479 (7)	0.0730 (10)	0.0376 (7)	0.0045 (7)	0.0163 (6)	−0.0002 (7)
C15	0.0472 (7)	0.0751 (11)	0.0328 (7)	0.0002 (7)	0.0136 (6)	−0.0001 (6)
C16	0.0478 (7)	0.0841 (11)	0.0325 (7)	0.0096 (8)	0.0129 (6)	0.0015 (7)
C17	0.0518 (8)	0.0882 (13)	0.0599 (10)	0.0095 (8)	0.0239 (7)	0.0147 (9)
C19	0.153 (2)	0.163 (3)	0.0547 (12)	−0.012 (2)	0.0391 (14)	0.0197 (14)
C20	0.0622 (9)	0.0682 (11)	0.0600 (10)	0.0118 (8)	0.0217 (8)	0.0020 (8)
C22	0.130 (2)	0.0972 (17)	0.0965 (17)	−0.0403 (15)	0.0254 (15)	−0.0151 (14)
C23	0.0840 (13)	0.1268 (18)	0.0789 (13)	0.0449 (12)	0.0398 (11)	0.0130 (12)
C25	0.0937 (14)	0.0846 (14)	0.0740 (13)	0.0009 (11)	0.0424 (11)	0.0053 (11)
C26	0.167 (3)	0.0907 (18)	0.132 (2)	0.0280 (17)	0.091 (2)	0.0252 (15)

Geometric parameters (Å, º)

O7—C15	1.3724 (19)	C9—C10	1.330 (3)
O7—C8	1.385 (2)	C9—H9	0.9300
O8—C8	1.196 (2)	C10—C16	1.447 (3)
O17—C17	1.189 (2)	C10—C23	1.497 (2)
O18—C17	1.319 (2)	C11—C12	1.362 (3)
O18—C19	1.447 (2)	C11—C16	1.394 (2)
O20—C20	1.195 (2)	C11—H11	0.9300
O21—C20	1.330 (2)	C12—C13	1.385 (2)
O21—C22	1.445 (2)	C12—H12	0.9300
O24—C25	1.378 (2)	C13—C14	1.380 (2)
O24—C13	1.395 (2)	C14—C15	1.384 (2)
O25—C25	1.186 (2)	C15—C16	1.398 (2)
N1—C5	1.328 (2)	C19—H191	0.9600
N1—N2	1.3525 (18)	C19—H192	0.9600
N1—C6	1.464 (2)	C19—H193	0.9600
N2—C3	1.326 (2)	C22—H221	0.9600
C3—C4	1.399 (2)	C22—H222	0.9600
C3—C17	1.488 (2)	C22—H223	0.9600
C4—C5	1.377 (2)	C23—H231	0.9600
C4—C20	1.461 (2)	C23—H232	0.9600
C5—H5	0.9300	C23—H233	0.9600
C6—C14	1.507 (2)	C25—C26	1.481 (3)
C6—H61	0.9700	C26—H261	0.9600
C6—H62	0.9700	C26—H262	0.9600
C8—C9	1.438 (3)	C26—H263	0.9600
C15—O7—C8	121.86 (14)	C13—C14—C6	122.05 (15)
C17—O18—C19	117.04 (19)	C15—C14—C6	120.99 (15)
C20—O21—C22	115.06 (16)	O7—C15—C14	115.75 (13)
C25—O24—C13	116.44 (14)	O7—C15—C16	121.08 (15)
C5—N1—N2	112.81 (12)	C14—C15—C16	123.17 (15)
C5—N1—C6	127.97 (14)	C11—C16—C15	116.86 (15)
N2—N1—C6	119.19 (13)	C11—C16—C10	124.88 (15)
C3—N2—N1	103.86 (13)	C15—C16—C10	118.26 (16)
N2—C3—C4	112.18 (13)	O17—C17—O18	125.31 (17)
N2—C3—C17	120.01 (15)	O17—C17—C3	124.60 (17)
C4—C3—C17	127.81 (15)	O18—C17—C3	110.08 (16)
C5—C4—C3	103.90 (14)	O18—C19—H191	109.5
C5—C4—C20	129.24 (16)	O18—C19—H192	109.5
C3—C4—C20	126.59 (15)	H191—C19—H192	109.5
N1—C5—C4	107.25 (14)	O18—C19—H193	109.5
N1—C5—H5	126.4	H191—C19—H193	109.5
C4—C5—H5	126.4	H192—C19—H193	109.5
N1—C6—C14	112.20 (12)	O20—C20—O21	123.56 (17)
N1—C6—H61	109.2	O20—C20—C4	124.17 (17)
C14—C6—H61	109.2	O21—C20—C4	112.24 (15)
N1—C6—H62	109.2	O21—C22—H221	109.5
C14—C6—H62	109.2	O21—C22—H222	109.5
H61—C6—H62	107.9	H221—C22—H222	109.5
O8—C8—O7	116.08 (18)	O21—C22—H223	109.5
O8—C8—C9	127.6 (2)	H221—C22—H223	109.5
O7—C8—C9	116.28 (17)	H222—C22—H223	109.5
C10—C9—C8	123.75 (18)	C10—C23—H231	109.5
C10—C9—H9	118.1	C10—C23—H232	109.5
C8—C9—H9	118.1	H231—C23—H232	109.5
C9—C10—C16	118.74 (16)	C10—C23—H233	109.5
C9—C10—C23	121.21 (19)	H231—C23—H233	109.5
C16—C10—C23	120.04 (19)	H232—C23—H233	109.5
C12—C11—C16	121.56 (15)	O25—C25—O24	122.1 (2)
C12—C11—H11	119.2	O25—C25—C26	127.0 (2)
C16—C11—H11	119.2	O24—C25—C26	110.93 (19)
C11—C12—C13	119.54 (17)	C25—C26—H261	109.5
C11—C12—H12	120.2	C25—C26—H262	109.5
C13—C12—H12	120.2	H261—C26—H262	109.5
C14—C13—C12	121.85 (17)	C25—C26—H263	109.5
C14—C13—O24	117.35 (14)	H261—C26—H263	109.5
C12—C13—O24	120.77 (16)	H262—C26—H263	109.5
C13—C14—C15	116.95 (14)
C5—N1—N2—C3	−0.41 (15)	C8—O7—C15—C14	177.64 (13)
C6—N1—N2—C3	177.95 (12)	C8—O7—C15—C16	−1.3 (2)
N1—N2—C3—C4	0.34 (16)	C13—C14—C15—O7	−177.57 (12)
N1—N2—C3—C17	−179.69 (13)	C6—C14—C15—O7	3.30 (19)
N2—C3—C4—C5	−0.16 (17)	C13—C14—C15—C16	1.3 (2)
C17—C3—C4—C5	179.88 (15)	C6—C14—C15—C16	−177.80 (13)
N2—C3—C4—C20	174.33 (14)	C12—C11—C16—C15	−1.8 (2)
C17—C3—C4—C20	−5.6 (3)	C12—C11—C16—C10	178.21 (14)
N2—N1—C5—C4	0.32 (16)	O7—C15—C16—C11	179.87 (12)
C6—N1—C5—C4	−177.86 (13)	C14—C15—C16—C11	1.0 (2)
C3—C4—C5—N1	−0.10 (16)	O7—C15—C16—C10	−0.14 (19)
C20—C4—C5—N1	−174.38 (15)	C14—C15—C16—C10	−178.99 (13)
C5—N1—C6—C14	103.58 (17)	C9—C10—C16—C11	−178.56 (15)
N2—N1—C6—C14	−74.50 (18)	C23—C10—C16—C11	1.5 (2)
C15—O7—C8—O8	−178.53 (15)	C9—C10—C16—C15	1.5 (2)
C15—O7—C8—C9	1.4 (2)	C23—C10—C16—C15	−178.52 (14)
O8—C8—C9—C10	179.90 (18)	C19—O18—C17—O17	−8.0 (3)
O7—C8—C9—C10	0.0 (2)	C19—O18—C17—C3	170.85 (18)
C8—C9—C10—C16	−1.4 (3)	N2—C3—C17—O17	−60.9 (2)
C8—C9—C10—C23	178.56 (16)	C4—C3—C17—O17	119.1 (2)
C16—C11—C12—C13	0.2 (2)	N2—C3—C17—O18	120.31 (17)
C11—C12—C13—C14	2.4 (2)	C4—C3—C17—O18	−59.7 (2)
C11—C12—C13—O24	−179.75 (14)	C22—O21—C20—O20	2.5 (3)
C25—O24—C13—C14	−112.27 (17)	C22—O21—C20—C4	−179.50 (18)
C25—O24—C13—C12	69.8 (2)	C5—C4—C20—O20	166.42 (18)
C12—C13—C14—C15	−3.1 (2)	C3—C4—C20—O20	−6.7 (3)
O24—C13—C14—C15	178.99 (12)	C5—C4—C20—O21	−11.6 (2)
C12—C13—C14—C6	176.07 (14)	C3—C4—C20—O21	175.32 (15)
O24—C13—C14—C6	−1.9 (2)	C13—O24—C25—O25	−5.7 (3)
N1—C6—C14—C13	99.95 (17)	C13—O24—C25—C26	173.25 (19)
N1—C6—C14—C15	−80.96 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O17^i	0.93	2.56	3.367 (2)	145
C12—H12···O20^i	0.93	2.49	3.349 (2)	154
C19—H193···O21^ii	0.96	2.57	3.436 (3)	150
C22—H222···O8^iii	0.96	2.47	3.421 (3)	172
C22—H223···O25^iv	0.96	2.55	3.264 (3)	131

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1/2, −y+1/2, −z+2; (iv) −x+1/2, y−1/2, −z+3/2.