Methyl 4-bromo-1,3-di­methyl­pyrazole-5-carboxyl­ate

Huo, F.; Yin, C.; Guo, W.; Xia, C.; Yang, P.

doi:10.1107/S160053680302525X

Methyl 4-bromo-1,3-dimethylpyrazole-5-carboxylate

F. Huo, C. Yin, W. Guo, C. Xia and P. Yang

The crystal structure of the title compound, C₇H₉BrN₂O₂, has been determined in the triclinic space group P $\overline 1$ . There are three molecules in the asymmetric unit, arranged with approximate threefold rotation symmetry, and the three pyrazole rings are almost coplanar. A bromine atom at the 4-position of the pyrazole ring provides the possibility for synthesis of substituted pyrazole derivatives. Packing is governed only by van der Waals interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302525X/na6264sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680302525X/na6264Isup2.hkl Contains datablock I

CCDC reference: 227916

checkCIF report

Key indicators

Single-crystal X-ray study
T = 183 K
Mean (C-C) = 0.006 Å
R factor = 0.035
wR factor = 0.079
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C4A
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C4B
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H4AB   ..  H6BB     =       2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         18
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C7 H9 Br N2 O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C7 H9 Br N2 O2

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Methyl 4-bromo-1,3-dimethylpyrazole-5-carboxylate top

Crystal data top

C₇H₉BrN₂O₂	Z = 6
M_r = 233.07	F(000) = 696
Triclinic, P1	D_x = 1.749 Mg m⁻³
Hall symbol: -P 1	Melting point: 330 K
a = 10.226 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.207 (2) Å	Cell parameters from 7285 reflections
c = 11.778 (2) Å	θ = 2.3–26.1°
α = 80.75 (3)°	µ = 4.61 mm⁻¹
β = 85.32 (3)°	T = 183 K
γ = 88.70 (3)°	Block, colorless
V = 1327.7 (5) Å³	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4564 independent reflections
Radiation source: fine-focus sealed tube	3338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→6
T_min = 0.226, T_max = 0.398	k = −13→11
5487 measured reflections	l = −14→13

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.033P)²] where P = (F_o² + 2F_c²)/3
4564 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.11390 (5)	−0.08230 (4)	1.21542 (3)	0.04118 (14)
Br1A	0.38798 (5)	−0.21076 (4)	1.05170 (3)	0.03978 (14)
Br1B	0.24342 (5)	0.08553 (4)	0.94187 (3)	0.03843 (14)
O1	−0.1568 (3)	−0.1736 (3)	1.5691 (2)	0.0522 (9)
O1A	0.7616 (3)	−0.4565 (3)	0.9746 (3)	0.0598 (9)
O1B	0.1422 (4)	0.4222 (3)	0.6587 (3)	0.0604 (10)
O2	0.0188 (3)	−0.2191 (3)	1.4585 (2)	0.0487 (8)
O2A	0.6140 (3)	−0.3204 (3)	0.9050 (2)	0.0432 (8)
O2B	0.1085 (3)	0.3251 (3)	0.8381 (2)	0.0465 (8)
N1	−0.1860 (4)	0.1279 (3)	1.3110 (3)	0.0398 (9)
N1A	0.5048 (4)	−0.4963 (3)	1.2741 (3)	0.0389 (9)
N1B	0.4418 (4)	0.1645 (3)	0.6299 (3)	0.0418 (9)
N2	−0.1897 (3)	0.0400 (3)	1.4034 (3)	0.0364 (9)
N2A	0.5921 (4)	−0.5033 (3)	1.1838 (3)	0.0373 (9)
N2B	0.3569 (4)	0.2571 (3)	0.6256 (3)	0.0371 (9)
C1	−0.0867 (4)	0.0993 (4)	1.2396 (3)	0.0353 (10)
C1A	0.4267 (4)	−0.4008 (4)	1.2425 (3)	0.0355 (10)
C1B	0.4144 (4)	0.0968 (4)	0.7338 (3)	0.0342 (10)
C2B	0.3108 (4)	0.1497 (4)	0.7926 (3)	0.0329 (10)
C2	−0.0278 (4)	−0.0079 (3)	1.2873 (3)	0.0304 (10)
C2A	0.4679 (4)	−0.3484 (3)	1.1291 (3)	0.0315 (10)
C3B	0.2742 (4)	0.2526 (3)	0.7223 (3)	0.0318 (10)
C3	−0.0951 (4)	−0.0451 (4)	1.3928 (3)	0.0330 (10)
C3A	0.5729 (4)	−0.4151 (3)	1.0932 (3)	0.0332 (10)
C4	−0.0516 (4)	0.1795 (3)	1.1246 (3)	0.0355 (10)
H4A	−0.1115	0.2493	1.1158	0.053*
H4B	−0.0594	0.1333	1.0616	0.053*
H4C	0.0388	0.2076	1.1224	0.053*
C4A	0.3165 (4)	−0.3647 (4)	1.3225 (3)	0.0383 (11)
H4AA	0.3137	−0.4203	1.3959	0.057*
H4AB	0.2332	−0.3679	1.2875	0.057*
H4AC	0.3307	−0.2822	1.3363	0.057*
C4B	0.4905 (4)	−0.0184 (4)	0.7695 (3)	0.0414 (11)
H4BA	0.5576	−0.0300	0.7078	0.062*
H4BB	0.4305	−0.0871	0.7837	0.062*
H4BC	0.5328	−0.0128	0.8401	0.062*
C5	−0.0835 (5)	−0.1512 (4)	1.4843 (3)	0.0360 (11)
C5A	0.6615 (5)	−0.4017 (4)	0.9866 (4)	0.0370 (11)
C5B	0.1694 (4)	0.3428 (4)	0.7336 (4)	0.0360 (10)
C6	0.0397 (5)	−0.3279 (4)	1.5414 (4)	0.0567 (14)
H6A	0.1173	−0.3715	1.5145	0.085*
H6B	−0.0373	−0.3799	1.5488	0.085*
H6C	0.0532	−0.3053	1.6165	0.085*
C6A	0.6960 (5)	−0.2913 (4)	0.7985 (3)	0.0522 (13)
H6AA	0.6513	−0.2309	0.7449	0.078*
H6AB	0.7128	−0.3646	0.7638	0.078*
H6AC	0.7795	−0.2586	0.8145	0.078*
C6B	−0.0014 (5)	0.4030 (4)	0.8598 (4)	0.0567 (14)
H6BA	−0.0376	0.3811	0.9399	0.085*
H6BB	−0.0690	0.3938	0.8076	0.085*
H6BC	0.0277	0.4872	0.8467	0.085*
C7	−0.2907 (4)	0.0487 (4)	1.4976 (3)	0.0498 (13)
H7A	−0.3437	0.1220	1.4781	0.075*
H7B	−0.2486	0.0524	1.5687	0.075*
H7C	−0.3472	−0.0223	1.5088	0.075*
C7A	0.6832 (5)	−0.6060 (4)	1.1936 (4)	0.0478 (12)
H7AA	0.6718	−0.6525	1.2716	0.072*
H7AB	0.7735	−0.5766	1.1785	0.072*
H7AC	0.6656	−0.6579	1.1372	0.072*
C7B	0.3688 (5)	0.3516 (4)	0.5233 (3)	0.0467 (13)
H7BA	0.4381	0.3289	0.4680	0.070*
H7BB	0.3910	0.4284	0.5464	0.070*
H7BC	0.2853	0.3605	0.4874	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0412 (3)	0.0430 (3)	0.0353 (2)	0.0136 (2)	0.0049 (2)	−0.00003 (19)
Br1A	0.0434 (3)	0.0390 (3)	0.0336 (2)	0.0128 (2)	−0.0022 (2)	0.00208 (19)
Br1B	0.0435 (3)	0.0394 (3)	0.0281 (2)	0.0061 (2)	0.0044 (2)	0.00303 (18)
O1	0.054 (2)	0.059 (2)	0.0376 (17)	−0.0019 (18)	0.0126 (17)	0.0028 (15)
O1A	0.049 (2)	0.074 (2)	0.055 (2)	0.026 (2)	0.0013 (18)	−0.0153 (18)
O1B	0.081 (3)	0.050 (2)	0.0463 (19)	0.0242 (19)	−0.0143 (19)	0.0064 (16)
O2	0.060 (2)	0.0412 (18)	0.0385 (17)	0.0075 (17)	0.0013 (17)	0.0083 (14)
O2A	0.047 (2)	0.0475 (19)	0.0334 (16)	0.0043 (16)	0.0033 (15)	−0.0049 (14)
O2B	0.047 (2)	0.0443 (18)	0.0447 (18)	0.0148 (16)	0.0021 (16)	−0.0015 (15)
N1	0.041 (2)	0.035 (2)	0.042 (2)	0.0041 (18)	0.0002 (19)	−0.0051 (17)
N1A	0.044 (2)	0.034 (2)	0.038 (2)	0.0064 (19)	−0.0044 (19)	−0.0034 (17)
N1B	0.052 (3)	0.034 (2)	0.037 (2)	0.0038 (19)	0.0064 (19)	−0.0058 (17)
N2	0.036 (2)	0.039 (2)	0.0344 (19)	0.0020 (18)	0.0028 (18)	−0.0096 (17)
N2A	0.041 (2)	0.030 (2)	0.042 (2)	0.0082 (18)	−0.0091 (19)	−0.0083 (17)
N2B	0.051 (3)	0.030 (2)	0.0292 (19)	−0.0061 (19)	−0.0022 (19)	0.0000 (15)
C1	0.034 (3)	0.036 (3)	0.036 (2)	0.003 (2)	−0.002 (2)	−0.0065 (19)
C1A	0.034 (3)	0.031 (2)	0.041 (2)	0.002 (2)	−0.007 (2)	−0.0027 (19)
C1B	0.039 (3)	0.033 (2)	0.029 (2)	−0.001 (2)	0.003 (2)	−0.0036 (19)
C2	0.030 (2)	0.032 (2)	0.029 (2)	0.003 (2)	0.000 (2)	−0.0063 (18)
C2A	0.033 (3)	0.030 (2)	0.032 (2)	0.002 (2)	−0.009 (2)	−0.0040 (18)
C2B	0.044 (3)	0.036 (2)	0.0187 (19)	−0.010 (2)	0.000 (2)	−0.0014 (18)
C3	0.032 (3)	0.033 (2)	0.036 (2)	0.000 (2)	−0.004 (2)	−0.0095 (19)
C3A	0.039 (3)	0.027 (2)	0.035 (2)	0.003 (2)	−0.012 (2)	−0.0076 (19)
C3B	0.037 (3)	0.030 (2)	0.029 (2)	−0.002 (2)	−0.007 (2)	−0.0043 (18)
C4	0.035 (3)	0.034 (2)	0.035 (2)	0.010 (2)	−0.002 (2)	−0.0007 (19)
C4A	0.048 (3)	0.037 (2)	0.027 (2)	0.009 (2)	−0.002 (2)	0.0024 (18)
C4B	0.047 (3)	0.036 (3)	0.037 (2)	0.002 (2)	0.013 (2)	−0.0034 (19)
C5	0.041 (3)	0.035 (3)	0.033 (2)	−0.003 (2)	−0.007 (2)	−0.007 (2)
C5A	0.038 (3)	0.035 (3)	0.041 (3)	0.006 (2)	−0.006 (2)	−0.015 (2)
C5B	0.041 (3)	0.032 (2)	0.036 (2)	−0.001 (2)	−0.010 (2)	−0.006 (2)
C6	0.073 (4)	0.042 (3)	0.048 (3)	0.006 (3)	−0.005 (3)	0.012 (2)
C6A	0.055 (3)	0.064 (3)	0.036 (2)	−0.001 (3)	0.010 (2)	−0.010 (2)
C6B	0.048 (3)	0.050 (3)	0.070 (3)	0.018 (3)	−0.003 (3)	−0.008 (3)
C7	0.046 (3)	0.060 (3)	0.045 (3)	0.006 (3)	0.012 (2)	−0.022 (2)
C7A	0.054 (3)	0.032 (3)	0.060 (3)	0.017 (2)	−0.014 (3)	−0.011 (2)
C7B	0.066 (4)	0.042 (3)	0.028 (2)	−0.008 (3)	−0.004 (2)	0.007 (2)

Geometric parameters (Å, º) top

Br1—C2	1.866 (4)	O2A—C6A	1.446 (5)
N1—C1	1.331 (5)	C4A—H4AA	0.9800
C1—C2	1.389 (5)	C4A—H4AB	0.9800
C2—C3	1.378 (5)	C4A—H4AC	0.9800
N2—C3	1.356 (5)	C6A—H6AA	0.9800
N1—N2	1.344 (4)	C6A—H6AB	0.9800
C1—C4	1.522 (5)	C6A—H6AC	0.9800
C3—C5	1.480 (5)	C7A—H7AA	0.9800
N2—C7	1.466 (5)	C7A—H7AB	0.9800
O1—C5	1.195 (5)	C7A—H7AC	0.9800
O2—C5	1.324 (5)	Br1B—C2B	1.871 (4)
O2—C6	1.457 (4)	N1B—C1B	1.345 (5)
C4—H4A	0.9800	C1B—C2B	1.392 (6)
C4—H4B	0.9800	C2B—C3B	1.371 (5)
C4—H4C	0.9800	N2B—C3B	1.357 (5)
C6—H6A	0.9800	N1B—N2B	1.335 (5)
C6—H6B	0.9800	C1B—C4B	1.511 (5)
C6—H6C	0.9800	C3B—C5B	1.469 (6)
C7—H7A	0.9800	O1B—C5B	1.193 (5)
C7—H7B	0.9800	O2B—C5B	1.320 (5)
C7—H7C	0.9800	O2B—C6B	1.439 (5)
Br1A—C2A	1.869 (4)	N2B—C7B	1.469 (4)
N1A—C1A	1.343 (5)	C4B—H4BA	0.9800
C1A—C2A	1.405 (5)	C4B—H4BB	0.9800
C2A—C3A	1.371 (6)	C4B—H4BC	0.9800
N2A—C3A	1.357 (5)	C6B—H6BA	0.9800
N1A—N2A	1.342 (5)	C6B—H6BB	0.9800
C1A—C4A	1.500 (6)	C6B—H6BC	0.9800
C3A—C5A	1.477 (6)	C7B—H7BA	0.9800
N2A—C7A	1.460 (5)	C7B—H7BB	0.9800
O1A—C5A	1.192 (5)	C7B—H7BC	0.9800
O2A—C5A	1.329 (5)

C2—C1—C4	129.0 (4)	H4BA—C4B—H4BB	109.5
N1—C1—C4	121.1 (4)	C1B—C4B—H4BC	109.5
C3—C2—Br1	129.0 (3)	H4BA—C4B—H4BC	109.5
C1—C2—Br1	124.3 (3)	H4BB—C4B—H4BC	109.5
C2—C3—C5	133.8 (4)	C1A—C4A—H4AA	109.5
N2—C3—C5	120.8 (4)	C1A—C4A—H4AB	109.5
C3—N2—C7	130.1 (4)	H4AA—C4A—H4AB	109.5
N1—N2—C7	117.8 (3)	C1A—C4A—H4AC	109.5
C5—O2—C6	115.8 (4)	H4AA—C4A—H4AC	109.5
N1—N2—C3	112.1 (3)	H4AB—C4A—H4AC	109.5
N1—C1—C2	109.9 (4)	C1—C4—H4A	109.5
C3—C2—C1	106.7 (4)	C1—C4—H4B	109.5
C1—N1—N2	105.9 (3)	H4A—C4—H4B	109.5
N2—C3—C2	105.3 (3)	C1—C4—H4C	109.5
O1—C5—O2	124.5 (4)	H4A—C4—H4C	109.5
O1—C5—C3	125.0 (4)	H4B—C4—H4C	109.5
O2—C5—C3	110.5 (4)	O2B—C6B—H6BA	109.5
C2A—C1A—C4A	129.8 (4)	O2B—C6B—H6BB	109.5
N1A—C1A—C4A	121.7 (4)	H6BA—C6B—H6BB	109.5
C3A—C2A—Br1A	129.8 (3)	O2B—C6B—H6BC	109.5
C1A—C2A—Br1A	122.8 (3)	H6BA—C6B—H6BC	109.5
C2A—C3A—C5A	132.9 (4)	H6BB—C6B—H6BC	109.5
N2A—C3A—C5A	121.4 (4)	O2A—C6A—H6AA	109.5
C3A—N2A—C7A	130.4 (4)	O2A—C6A—H6AB	109.5
N1A—N2A—C7A	117.3 (3)	H6AA—C6A—H6AB	109.5
C5A—O2A—C6A	116.6 (4)	O2A—C6A—H6AC	109.5
N1A—N2A—C3A	112.1 (3)	H6AA—C6A—H6AC	109.5
N1A—C1A—C2A	108.4 (4)	H6AB—C6A—H6AC	109.5
C3A—C2A—C1A	107.4 (4)	O2—C6—H6A	109.5
N2A—N1A—C1A	106.6 (3)	O2—C6—H6B	109.5
N2A—C3A—C2A	105.5 (4)	H6A—C6—H6B	109.5
O1A—C5A—O2A	124.3 (4)	O2—C6—H6C	109.5
O1A—C5A—C3A	125.0 (4)	H6A—C6—H6C	109.5
O2A—C5A—C3A	110.7 (4)	H6B—C6—H6C	109.5
C2B—C1B—C4B	130.1 (3)	N2B—C7B—H7BA	109.5
N1B—C1B—C4B	120.6 (4)	N2B—C7B—H7BB	109.5
C3B—C2B—Br1B	129.3 (3)	H7BA—C7B—H7BB	109.5
C1B—C2B—Br1B	123.2 (3)	N2B—C7B—H7BC	109.5
C2B—C3B—C5B	133.2 (4)	H7BA—C7B—H7BC	109.5
N2B—C3B—C5B	122.3 (4)	H7BB—C7B—H7BC	109.5
C3B—N2B—C7B	128.8 (4)	N2—C7—H7A	109.5
N1B—N2B—C7B	117.7 (4)	N2—C7—H7B	109.5
C5B—O2B—C6B	117.3 (3)	H7A—C7—H7B	109.5
N1B—N2B—C3B	113.4 (3)	N2—C7—H7C	109.5
N1B—C1B—C2B	109.3 (4)	H7A—C7—H7C	109.5
C3B—C2B—C1B	107.5 (3)	H7B—C7—H7C	109.5
N2B—N1B—C1B	105.3 (3)	N2A—C7A—H7AA	109.5
N2B—C3B—C2B	104.5 (4)	N2A—C7A—H7AB	109.5
O1B—C5B—O2B	124.0 (4)	H7AA—C7A—H7AB	109.5
O1B—C5B—C3B	124.8 (4)	N2A—C7A—H7AC	109.5
O2B—C5B—C3B	111.2 (4)	H7AA—C7A—H7AC	109.5
C1B—C4B—H4BA	109.5	H7AB—C7A—H7AC	109.5
C1B—C4B—H4BB	109.5

C1—N1—N2—C3	−0.3 (4)	C7—N2—C3—C2	−179.7 (4)
C1—N1—N2—C7	179.6 (3)	N1—N2—C3—C5	−178.8 (3)
C1A—N1A—N2A—C3A	−0.4 (5)	C7—N2—C3—C5	1.3 (6)
C1A—N1A—N2A—C7A	−175.7 (3)	C1—C2—C3—N2	0.0 (4)
C1B—N1B—N2B—C3B	−0.3 (5)	Br1—C2—C3—N2	−179.2 (3)
C1B—N1B—N2B—C7B	176.4 (3)	C1—C2—C3—C5	178.8 (4)
N2A—N1A—C1A—C2A	0.2 (5)	Br1—C2—C3—C5	−0.4 (7)
N2A—N1A—C1A—C4A	−179.9 (4)	N1A—N2A—C3A—C2A	0.4 (5)
N2—N1—C1—C2	0.3 (5)	C7A—N2A—C3A—C2A	175.0 (4)
N2—N1—C1—C4	−179.6 (3)	N1A—N2A—C3A—C5A	177.0 (3)
N2B—N1B—C1B—C2B	0.2 (5)	C7A—N2A—C3A—C5A	−8.5 (7)
N2B—N1B—C1B—C4B	179.2 (4)	C1A—C2A—C3A—N2A	−0.3 (5)
N1B—C1B—C2B—C3B	0.0 (5)	Br1A—C2A—C3A—N2A	178.5 (3)
C4B—C1B—C2B—C3B	−178.9 (4)	C1A—C2A—C3A—C5A	−176.2 (4)
N1B—C1B—C2B—Br1B	−178.9 (3)	Br1A—C2A—C3A—C5A	2.5 (7)
C4B—C1B—C2B—Br1B	2.2 (6)	C6A—O2A—C5A—O1A	−5.1 (6)
N1—C1—C2—C3	−0.2 (5)	C6A—O2A—C5A—C3A	175.4 (3)
C4—C1—C2—C3	179.7 (4)	N2A—C3A—C5A—O1A	−7.7 (7)
N1—C1—C2—Br1	179.1 (3)	C2A—C3A—C5A—O1A	167.7 (5)
C4—C1—C2—Br1	−1.1 (6)	N2A—C3A—C5A—O2A	171.8 (3)
N1A—C1A—C2A—C3A	0.1 (5)	C2A—C3A—C5A—O2A	−12.8 (6)
C4A—C1A—C2A—C3A	−179.9 (4)	C6—O2—C5—O1	0.2 (6)
N1A—C1A—C2A—Br1A	−178.8 (3)	C6—O2—C5—C3	−179.1 (3)
C4A—C1A—C2A—Br1A	1.2 (6)	N2—C3—C5—O1	3.6 (6)
N1B—N2B—C3B—C2B	0.4 (5)	C2—C3—C5—O1	−175.0 (4)
C7B—N2B—C3B—C2B	−175.9 (4)	N2—C3—C5—O2	−177.1 (4)
N1B—N2B—C3B—C5B	−177.4 (4)	C2—C3—C5—O2	4.2 (6)
C7B—N2B—C3B—C5B	6.4 (6)	C6B—O2B—C5B—O1B	3.3 (6)
C1B—C2B—C3B—N2B	−0.2 (4)	C6B—O2B—C5B—C3B	−176.7 (3)
Br1B—C2B—C3B—N2B	178.6 (3)	N2B—C3B—C5B—O1B	4.8 (7)
C1B—C2B—C3B—C5B	177.1 (4)	C2B—C3B—C5B—O1B	−172.2 (5)
Br1B—C2B—C3B—C5B	−4.0 (7)	N2B—C3B—C5B—O2B	−175.1 (3)
N1—N2—C3—C2	0.1 (4)	C2B—C3B—C5B—O2B	7.9 (7)

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Methyl 4-bromo-1,3-di­methyl­pyrazole-5-carboxyl­ate

Supporting information

Key indicators

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Methyl 4-bromo-1,3-dimethylpyrazole-5-carboxylate