2,6-Di­bromo-3,4,5-tri­meth­oxy­benzoic acid

The previously unknown crystal structure of 2,6-di­bromo-3,4,5-tri­meth­oxy­benzoic acid was determined employing state-of-the-art Hirshfeld atom refinement and the crystal packing was analysed using Hirshfeld surface analysis.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• R factor = 0.053
• wR factor = 0.123
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.008 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.441 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          4 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0100 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0100 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         10 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         63 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        1.0 Low
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          2 Check
PLAT977_ALERT_2_G Check Negative Difference Density on H00F      .      -0.25 eA-3
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info
PLAT979_ALERT_1_G NoSpherA2 Scattering Factors Used ..............     Please Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  16 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: CrysAlis PRO 1.171.43.36a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.43.36a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.43.36a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015); program(s) used to refine structure: olex2.refine 1.5-alpha (Bourhis et al., 2015), NoSpherA2 (Kleemiss et al., 2021); molecular graphics: Olex2 1.5-alpha (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2,6-Dibromo-3,4,5-trimethoxybenzoic acid

Crystal data

C10H10Br2O5	F(000) = 718.856
Mr = 370.00	Dx = 1.875 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.4047 (9) Å	Cell parameters from 1911 reflections
b = 7.1107 (3) Å	θ = 3.1–28.8°
c = 16.8997 (13) Å	µ = 6.19 mm^−1
β = 107.009 (8)°	T = 100 K
V = 1310.54 (16) Å^3	Block, clear colourless
Z = 4	0.08 × 0.06 × 0.03 mm

Data collection

SuperNova, Dualflex, AtlasS2 diffractometer	3245 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2254 reflections with I ≥ 2u(I)
Mirror monochromator	Rint = 0.084
Detector resolution: 5.2548 pixels mm^-1	θmax = 28.3°, θmin = 3.1°
ω scans	h = −17→19
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	k = −12→6
Tmin = 0.749, Tmax = 0.855	l = −28→28
18764 measured reflections

Refinement

Refinement on F^2	4 constraints
Least-squares matrix: full	Primary atom site location: dual
R[F^2 > 2σ(F^2)] = 0.053	Only H-atom displacement parameters refined
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0395P)^2 + 3.4625P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.0002
3245 reflections	Δρmax = 1.25 e Å^−3
218 parameters	Δρmin = −1.48 e Å^−3
63 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.86638 (5)	0.67372 (7)	0.45104 (4)	0.03398 (18)
Br2	0.43161 (5)	0.68854 (7)	0.17096 (3)	0.03341 (18)
O1	0.6558 (4)	0.9831 (5)	0.3032 (2)	0.0315 (9)
H1	0.692 (6)	1.0810 (6)	0.277 (4)	0.04 (2)
O2	0.7570 (4)	0.7934 (5)	0.2410 (3)	0.0384 (11)
O3	0.7246 (5)	0.3480 (5)	0.5004 (3)	0.0468 (12)
O4	0.5037 (4)	0.1913 (5)	0.4131 (3)	0.0442 (12)
O5	0.3643 (4)	0.3576 (5)	0.2669 (3)	0.0484 (13)
C4	0.6357 (4)	0.6586 (6)	0.3198 (3)	0.0200 (10)
C5	0.7054 (5)	0.5773 (7)	0.3932 (3)	0.0278 (12)
C3	0.5234 (5)	0.5822 (7)	0.2773 (4)	0.0284 (12)
C6	0.6606 (6)	0.4204 (7)	0.4262 (3)	0.0312 (13)
C2	0.4771 (5)	0.4239 (7)	0.3079 (4)	0.0319 (13)
C7	0.6884 (5)	0.8184 (7)	0.2838 (3)	0.0261 (12)
C1	0.5451 (6)	0.3442 (7)	0.3827 (4)	0.0300 (13)
C8	0.7911 (7)	0.1815 (8)	0.4937 (4)	0.0472 (17)
H00a	0.852 (3)	0.2105 (16)	0.457 (2)	0.056 (11)
H00b	0.844 (3)	0.136 (3)	0.5545 (5)	0.057 (10)
H00c	0.7277 (7)	0.0722 (18)	0.465 (2)	0.048 (10)
C10	0.3618 (7)	0.1753 (8)	0.2314 (5)	0.0523 (19)
H00d	0.2696 (10)	0.142 (3)	0.195 (2)	0.066 (11)
H00e	0.421 (3)	0.173 (2)	0.192 (2)	0.061 (11)
H00f	0.393 (4)	0.0726 (11)	0.2799 (5)	0.060 (11)
C9	0.4330 (7)	0.2341 (9)	0.4679 (5)	0.056 (2)
H00g	0.359 (2)	0.326 (5)	0.4373 (10)	0.062 (10)
H00h	0.397 (3)	0.1060 (11)	0.485 (2)	0.052 (10)
H00i	0.4904 (11)	0.302 (5)	0.5224 (12)	0.072 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0308 (3)	0.0207 (3)	0.0382 (4)	0.0033 (2)	−0.0091 (2)	−0.0047 (2)
Br2	0.0382 (4)	0.0181 (3)	0.0312 (3)	0.0032 (2)	−0.0097 (2)	−0.0045 (2)
O1	0.043 (2)	0.0208 (19)	0.038 (2)	−0.0014 (17)	0.0242 (19)	0.0003 (16)
H1	0.08 (4)	0.03 (3)	0.04 (3)	−0.024 (13)	0.033 (17)	−0.006 (13)
O2	0.061 (3)	0.0176 (19)	0.056 (3)	0.0006 (18)	0.047 (2)	0.0001 (18)
O3	0.083 (4)	0.029 (2)	0.031 (2)	0.010 (2)	0.021 (2)	0.0072 (18)
O4	0.068 (3)	0.021 (2)	0.062 (3)	0.0039 (19)	0.048 (3)	0.0028 (19)
O5	0.027 (2)	0.026 (2)	0.089 (4)	−0.0041 (17)	0.013 (2)	−0.007 (2)
C4	0.023 (3)	0.015 (2)	0.025 (3)	−0.0035 (19)	0.012 (2)	−0.0007 (18)
C5	0.035 (3)	0.022 (3)	0.028 (3)	0.004 (2)	0.012 (2)	0.000 (2)
C3	0.026 (3)	0.019 (3)	0.040 (3)	−0.002 (2)	0.009 (2)	−0.002 (2)
C6	0.049 (4)	0.020 (3)	0.028 (3)	0.002 (2)	0.018 (3)	0.004 (2)
C2	0.026 (3)	0.024 (3)	0.050 (4)	−0.005 (2)	0.016 (3)	−0.001 (2)
C7	0.036 (3)	0.014 (2)	0.035 (3)	0.003 (2)	0.022 (2)	−0.001 (2)
C1	0.043 (3)	0.015 (2)	0.040 (3)	−0.001 (2)	0.026 (3)	0.003 (2)
C8	0.068 (5)	0.028 (3)	0.039 (4)	0.009 (3)	0.006 (3)	0.008 (3)
H00a	0.069 (13)	0.05 (3)	0.041 (11)	0.005 (8)	0.006 (6)	0.012 (7)
H00b	0.072 (15)	0.05 (2)	0.042 (7)	0.006 (8)	0.005 (5)	0.014 (5)
H00c	0.066 (17)	0.031 (15)	0.040 (12)	0.011 (8)	0.008 (6)	0.008 (6)
C10	0.050 (5)	0.028 (3)	0.077 (6)	−0.005 (3)	0.016 (4)	−0.009 (3)
H00d	0.054 (7)	0.06 (3)	0.082 (14)	−0.012 (5)	0.015 (5)	−0.003 (8)
H00e	0.053 (10)	0.05 (3)	0.078 (13)	−0.008 (7)	0.016 (6)	−0.010 (8)
H00f	0.063 (13)	0.036 (19)	0.079 (14)	−0.003 (7)	0.018 (6)	−0.007 (8)
C9	0.076 (6)	0.036 (4)	0.081 (6)	0.010 (3)	0.063 (5)	0.010 (4)
H00g	0.082 (12)	0.038 (11)	0.09 (2)	0.012 (5)	0.059 (8)	0.008 (6)
H00h	0.081 (17)	0.033 (9)	0.073 (19)	0.012 (6)	0.070 (8)	0.003 (6)
H00i	0.10 (2)	0.041 (12)	0.092 (12)	0.008 (6)	0.051 (8)	0.007 (6)

Geometric parameters (Å, º)

Br1—C5	1.935 (6)	C5—C6	1.408 (7)
Br2—C3	1.948 (6)	C3—C2	1.405 (7)
O1—C7	1.299 (6)	C6—C1	1.415 (8)
O2—C7	1.224 (6)	C2—C1	1.395 (8)
O3—C6	1.354 (7)	C8—H00a	1.0770
O3—C8	1.429 (7)	C8—H00b	1.0770
O4—C1	1.346 (6)	C8—H00c	1.0770
O4—C9	1.427 (7)	C10—H00d	1.0770
O5—C2	1.355 (7)	C10—H00e	1.0770
O5—C10	1.425 (7)	C10—H00f	1.0770
C4—C5	1.388 (7)	C9—H00g	1.0770
C4—C3	1.383 (7)	C9—H00h	1.0770
C4—C7	1.496 (7)	C9—H00i	1.0770
C1—C2—C3	119.3 (5)	C8—O3—C6	113.4 (5)
C1—C2—O5	121.0 (5)	C9—O4—C1	113.8 (4)
C1—C6—C5	119.2 (5)	H00a—C8—O3	109.5
C1—C6—O3	120.2 (5)	H00b—C8—H00a	109.5
C10—O5—C2	115.5 (5)	H00b—C8—O3	109.5
C2—C1—C6	120.1 (5)	H00c—C8—H00b	109.5
C2—C1—O4	120.6 (6)	H00c—C8—H00a	109.5
C2—C3—C4	120.9 (5)	H00c—C8—O3	109.5
C2—C3—Br2	119.5 (4)	H00d—C10—O5	109.5
C3—C2—O5	119.6 (5)	H00e—C10—H00d	109.5
C3—C4—C5	120.1 (5)	H00e—C10—O5	109.5
C4—C7—O2	122.1 (4)	H00f—C10—H00e	109.5
C4—C7—O1	113.8 (4)	H00f—C10—H00d	109.5
C4—C3—Br2	119.5 (4)	H00f—C10—O5	109.5
C4—C5—Br1	121.0 (4)	H00g—C9—O4	109.5
C5—C6—O3	120.5 (6)	H00h—C9—H00g	109.5
C6—C1—O4	119.3 (5)	H00h—C9—O4	109.5
C6—C5—C4	120.3 (5)	H00i—C9—H00h	109.5
C6—C5—Br1	118.8 (4)	H00i—C9—H00g	109.5
C7—C4—C3	120.5 (5)	H00i—C9—O4	109.5
C7—C4—C5	119.1 (5)	O2—C7—O1	124.0 (5)
C7—O1—H1	109.5
Br1—C5—C4—C3	176.9 (4)	O3—C6—C5—C4	−175.7 (5)
Br1—C5—C4—C7	2.2 (5)	O3—C6—C1—O4	−4.6 (6)
Br1—C5—C6—O3	5.3 (5)	O3—C6—C1—C2	177.3 (5)
Br1—C5—C6—C1	−177.5 (4)	O4—C1—C6—C5	178.3 (5)
Br2—C3—C4—C5	−176.2 (4)	O4—C1—C2—O5	4.4 (6)
Br2—C3—C4—C7	−1.7 (5)	O4—C1—C2—C3	−179.2 (5)
Br2—C3—C2—O5	−5.8 (5)	O5—C2—C3—C4	176.9 (5)
Br2—C3—C2—C1	177.8 (4)	O5—C2—C1—C6	−177.5 (5)
O1—C7—C4—C5	−96.1 (5)	C4—C5—C6—C1	1.4 (6)
O1—C7—C4—C3	89.3 (5)	C4—C3—C2—C1	0.5 (6)
O2—C7—C4—C5	83.0 (6)	C5—C6—C1—C2	0.2 (6)
O2—C7—C4—C3	−91.5 (6)	C3—C2—C1—C6	−1.2 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.98 (5)	1.68 (3)	2.617 (5)	160 (5)

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.