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The title compound, C13H10Br2O2, was obtained during the synthesis of azulene derivatives. There are two independent mol­ecules in the asymmetric unit. The azulene frameworks of the mol­ecules are planar, with mean deviations of 0.01 and 0.02 Å from the ring planes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001972/ob6470sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001972/ob6470Isup2.hkl
Contains datablock I

CCDC reference: 264092

Key indicators

  • Single-crystal X-ray study
  • T = 95 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.042
  • wR factor = 0.092
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C13 H10 Br2 O2
Alert level G 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 28.30 From the CIF: _reflns_number_total 5943 Count of symmetry unique reflns 3063 Completeness (_total/calc) 194.03% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2880 Fraction of Friedel pairs measured 0.940 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.

Ethyl 1,3-dibromoazulene-6-carboxylate top
Crystal data top
C13H10Br2O2Dx = 1.964 Mg m3
Mr = 358.03Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 12806 reflections
a = 17.032 (2) Åθ = 2.5–28.3°
b = 3.9694 (5) ŵ = 6.68 mm1
c = 35.819 (5) ÅT = 95 K
V = 2421.6 (5) Å3Needle, dark green
Z = 80.27 × 0.08 × 0.08 mm
F(000) = 1392
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
5943 independent reflections
Radiation source: fine-focus sealed tube5714 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 28.3°, θmin = 2.3°
Absorption correction: numerical
(SMART; Bruker, 2001)
h = 2213
Tmin = 0.266, Tmax = 0.617k = 55
15805 measured reflectionsl = 4747
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0295P)2 + 8.7967P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.002
5943 reflectionsΔρmax = 1.01 e Å3
310 parametersΔρmin = 1.59 e Å3
1 restraintAbsolute structure: Flack (1983), 2880 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.141 (13)
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
xyzUiso*/Ueq
Br10.47259 (3)0.13298 (15)0.852525 (17)0.02002 (12)
Br20.77321 (3)0.07110 (13)0.780198 (14)0.01718 (11)
O10.8739 (2)0.7617 (11)0.95558 (11)0.0193 (8)
O20.7596 (2)0.9149 (11)0.98170 (12)0.0231 (9)
C10.5809 (3)0.1495 (16)0.84250 (14)0.0184 (11)
C20.6169 (3)0.0111 (13)0.81180 (15)0.0155 (10)
H20.59150.10190.79180.019*
C30.6976 (3)0.0665 (13)0.81533 (14)0.0131 (10)
C3A0.7140 (3)0.2356 (13)0.84865 (14)0.0129 (9)
C40.7868 (3)0.3215 (14)0.86236 (13)0.0150 (10)
H40.82970.26410.84670.018*
C50.8074 (3)0.4805 (14)0.89582 (16)0.0174 (11)
H50.86200.50760.90020.021*
C60.7570 (3)0.6053 (14)0.92384 (15)0.0164 (10)
C70.6752 (3)0.6006 (13)0.92544 (15)0.0168 (10)
H70.65270.70590.94670.020*
C80.6222 (3)0.4632 (14)0.90026 (14)0.0145 (10)
H80.56840.48940.90670.017*
C8A0.6359 (3)0.2947 (13)0.86730 (14)0.0126 (10)
C90.7956 (3)0.7755 (14)0.95702 (15)0.0176 (10)
C100.9162 (3)0.9324 (14)0.98557 (16)0.0182 (11)
H10A0.90910.81111.00950.022*
H10B0.89691.16600.98860.022*
C111.0017 (4)0.9321 (16)0.97424 (17)0.0225 (12)
H11A1.00671.02020.94880.034*
H11B1.02210.70140.97510.034*
H11C1.03171.07450.99140.034*
Br1'0.76392 (3)0.45833 (15)0.679699 (16)0.02267 (13)
Br2'0.46196 (3)0.51438 (14)0.753743 (15)0.01849 (11)
O1'0.3777 (2)0.3501 (10)0.57823 (10)0.0192 (8)
O2'0.4941 (2)0.4232 (12)0.55007 (12)0.0241 (9)
C1'0.6567 (3)0.3833 (13)0.68925 (15)0.0148 (10)
C2'0.6188 (3)0.5020 (13)0.72134 (17)0.0181 (11)
H2'0.64240.62160.74140.022*
C3'0.5391 (3)0.4107 (13)0.71836 (15)0.0153 (10)
C3A'0.5262 (3)0.2405 (13)0.68476 (14)0.0157 (10)
C4'0.4554 (3)0.1209 (14)0.67154 (15)0.0154 (10)
H4'0.41170.15400.68760.018*
C5'0.4388 (3)0.0411 (14)0.63804 (16)0.0164 (11)
H5'0.38520.09800.63430.020*
C6'0.4898 (3)0.1327 (13)0.60894 (15)0.0150 (10)
C7'0.5707 (3)0.0751 (15)0.60603 (16)0.0196 (11)
H7'0.59470.15590.58380.024*
C8'0.6207 (3)0.0835 (14)0.63101 (16)0.0177 (11)
H8'0.67400.09640.62340.021*
C8A'0.6040 (3)0.2261 (14)0.66548 (14)0.0163 (11)
C9'0.4557 (3)0.3172 (13)0.57583 (15)0.0160 (10)
C10'0.3395 (3)0.5287 (15)0.54780 (15)0.0195 (11)
H10C0.34110.39170.52470.023*
H10D0.36660.74510.54300.023*
C11'0.2562 (4)0.5910 (18)0.55930 (17)0.0268 (13)
H11D0.25540.73590.58150.040*
H11E0.23080.37590.56510.040*
H11F0.22800.70210.53890.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0091 (2)0.0247 (3)0.0263 (3)0.0034 (2)0.0022 (2)0.0016 (2)
Br20.0133 (2)0.0188 (3)0.0194 (3)0.0013 (2)0.0025 (2)0.0034 (2)
O10.0145 (17)0.025 (2)0.0183 (18)0.0020 (16)0.0038 (14)0.0037 (16)
O20.0203 (19)0.031 (2)0.018 (2)0.0005 (18)0.0017 (16)0.0058 (17)
C10.012 (2)0.029 (3)0.014 (3)0.000 (2)0.0024 (17)0.000 (2)
C20.017 (3)0.015 (3)0.015 (2)0.004 (2)0.0017 (19)0.0029 (18)
C30.012 (2)0.012 (2)0.015 (2)0.0038 (19)0.0011 (18)0.0005 (19)
C3A0.0096 (19)0.016 (2)0.013 (2)0.0015 (18)0.0027 (18)0.0066 (18)
C40.010 (2)0.023 (3)0.012 (2)0.003 (2)0.0012 (17)0.0038 (19)
C50.008 (2)0.018 (3)0.026 (3)0.001 (2)0.000 (2)0.002 (2)
C60.014 (2)0.021 (3)0.014 (2)0.004 (2)0.0021 (19)0.0026 (19)
C70.020 (3)0.015 (3)0.015 (2)0.001 (2)0.002 (2)0.001 (2)
C80.012 (2)0.016 (3)0.015 (2)0.002 (2)0.0026 (18)0.0033 (19)
C8A0.011 (2)0.009 (2)0.017 (2)0.0001 (19)0.0010 (17)0.0048 (18)
C90.019 (2)0.015 (3)0.019 (3)0.000 (2)0.000 (2)0.001 (2)
C100.020 (3)0.016 (3)0.019 (3)0.002 (2)0.000 (2)0.008 (2)
C110.022 (3)0.022 (3)0.024 (3)0.005 (2)0.001 (2)0.003 (2)
Br1'0.0125 (2)0.0256 (3)0.0300 (3)0.0045 (2)0.0027 (2)0.0011 (2)
Br2'0.0155 (2)0.0220 (3)0.0180 (2)0.0043 (2)0.0019 (2)0.0032 (2)
O1'0.0181 (18)0.021 (2)0.0182 (19)0.0002 (16)0.0028 (15)0.0051 (15)
O2'0.022 (2)0.029 (2)0.021 (2)0.0029 (18)0.0018 (17)0.0027 (17)
C1'0.011 (2)0.014 (2)0.020 (2)0.007 (2)0.0007 (18)0.0068 (19)
C2'0.014 (3)0.008 (2)0.032 (3)0.001 (2)0.000 (2)0.000 (2)
C3'0.010 (2)0.014 (2)0.021 (3)0.001 (2)0.0048 (19)0.000 (2)
C3A'0.015 (2)0.014 (2)0.017 (2)0.0013 (19)0.0009 (19)0.0025 (19)
C4'0.013 (2)0.016 (3)0.017 (2)0.005 (2)0.0033 (18)0.003 (2)
C5'0.013 (2)0.017 (3)0.019 (3)0.001 (2)0.002 (2)0.002 (2)
C6'0.018 (2)0.008 (2)0.019 (2)0.000 (2)0.0032 (19)0.0031 (19)
C7'0.018 (3)0.024 (3)0.017 (3)0.005 (2)0.001 (2)0.001 (2)
C8'0.015 (2)0.014 (3)0.024 (3)0.003 (2)0.003 (2)0.007 (2)
C8A'0.014 (2)0.014 (3)0.021 (3)0.004 (2)0.0020 (19)0.0042 (19)
C9'0.022 (3)0.011 (2)0.016 (2)0.002 (2)0.0014 (19)0.0007 (19)
C10'0.024 (3)0.023 (3)0.012 (2)0.000 (2)0.004 (2)0.003 (2)
C11'0.026 (3)0.037 (4)0.017 (3)0.004 (3)0.001 (2)0.007 (2)
Geometric parameters (Å, º) top
Br1—C11.881 (5)Br1'—C1'1.881 (5)
Br2—C31.882 (5)Br2'—C3'1.871 (5)
O1—C91.336 (6)O1'—C9'1.338 (7)
O1—C101.460 (6)O1'—C10'1.454 (6)
O2—C91.210 (7)O2'—C9'1.206 (7)
C1—C21.374 (8)C1'—C8A'1.386 (7)
C1—C8A1.413 (7)C1'—C2'1.400 (8)
C2—C31.397 (7)C2'—C3'1.409 (7)
C2—H20.9500C2'—H2'0.9500
C3—C3A1.398 (7)C3'—C3A'1.398 (8)
C3A—C41.376 (7)C3A'—C4'1.380 (7)
C3A—C8A1.507 (6)C3A'—C8A'1.495 (7)
C4—C51.399 (8)C4'—C5'1.390 (8)
C4—H40.9500C4'—H4'0.9500
C5—C61.410 (8)C5'—C6'1.405 (8)
C5—H50.9500C5'—H5'0.9500
C6—C71.394 (7)C6'—C7'1.401 (7)
C6—C91.517 (8)C6'—C9'1.510 (7)
C7—C81.388 (8)C7'—C8'1.386 (8)
C7—H70.9500C7'—H7'0.9500
C8—C8A1.377 (7)C8'—C8A'1.388 (8)
C8—H80.9500C8'—H8'0.9500
C10—C111.512 (8)C10'—C11'1.497 (8)
C10—H10A0.9900C10'—H10C0.9900
C10—H10B0.9900C10'—H10D0.9900
C11—H11A0.9800C11'—H11D0.9800
C11—H11B0.9800C11'—H11E0.9800
C11—H11C0.9800C11'—H11F0.9800
C9—O1—C10116.4 (4)C9'—O1'—C10'116.4 (4)
C2—C1—C8A111.8 (5)C8A'—C1'—C2'110.9 (5)
C2—C1—Br1125.2 (4)C8A'—C1'—Br1'126.0 (4)
C8A—C1—Br1123.0 (4)C2'—C1'—Br1'122.9 (4)
C1—C2—C3107.6 (5)C1'—C2'—C3'107.2 (5)
C1—C2—H2126.2C1'—C2'—H2'126.4
C3—C2—H2126.2C3'—C2'—H2'126.4
C2—C3—C3A110.5 (4)C3A'—C3'—C2'109.9 (5)
C2—C3—Br2124.5 (4)C3A'—C3'—Br2'125.4 (4)
C3A—C3—Br2125.0 (4)C2'—C3'—Br2'124.6 (4)
C4—C3A—C3127.2 (5)C4'—C3A'—C3'126.8 (5)
C4—C3A—C8A126.7 (5)C4'—C3A'—C8A'127.1 (5)
C3—C3A—C8A106.0 (4)C3'—C3A'—C8A'106.1 (4)
C3A—C4—C5130.0 (5)C3A'—C4'—C5'129.3 (5)
C3A—C4—H4115.0C3A'—C4'—H4'115.4
C5—C4—H4115.0C5'—C4'—H4'115.4
C4—C5—C6128.0 (5)C4'—C5'—C6'129.3 (5)
C4—C5—H5116.0C4'—C5'—H5'115.3
C6—C5—H5116.0C6'—C5'—H5'115.3
C7—C6—C5129.2 (5)C7'—C6'—C5'128.4 (5)
C7—C6—C9114.0 (5)C7'—C6'—C9'113.5 (5)
C5—C6—C9116.8 (5)C5'—C6'—C9'118.1 (5)
C8—C7—C6129.0 (5)C8'—C7'—C6'129.1 (5)
C8—C7—H7115.5C8'—C7'—H7'115.5
C6—C7—H7115.5C6'—C7'—H7'115.5
C8A—C8—C7129.6 (5)C7'—C8'—C8A'129.4 (5)
C8A—C8—H8115.2C7'—C8'—H8'115.3
C7—C8—H8115.2C8A'—C8'—H8'115.3
C8—C8A—C1128.6 (5)C1'—C8A'—C8'126.7 (5)
C8—C8A—C3A127.3 (5)C1'—C8A'—C3A'105.8 (5)
C1—C8A—C3A104.1 (4)C8'—C8A'—C3A'127.4 (5)
O2—C9—O1123.6 (5)O2'—C9'—O1'123.6 (5)
O2—C9—C6123.8 (5)O2'—C9'—C6'124.2 (5)
O1—C9—C6112.6 (5)O1'—C9'—C6'112.2 (4)
O1—C10—C11106.1 (4)O1'—C10'—C11'107.4 (5)
O1—C10—H10A110.5O1'—C10'—H10C110.2
C11—C10—H10A110.5C11'—C10'—H10C110.2
O1—C10—H10B110.5O1'—C10'—H10D110.2
C11—C10—H10B110.5C11'—C10'—H10D110.2
H10A—C10—H10B108.7H10C—C10'—H10D108.5
C10—C11—H11A109.5C10'—C11'—H11D109.5
C10—C11—H11B109.5C10'—C11'—H11E109.5
H11A—C11—H11B109.5H11D—C11'—H11E109.5
C10—C11—H11C109.5C10'—C11'—H11F109.5
H11A—C11—H11C109.5H11D—C11'—H11F109.5
H11B—C11—H11C109.5H11E—C11'—H11F109.5
C8A—C1—C2—C30.9 (7)C8A'—C1'—C2'—C3'1.3 (6)
Br1—C1—C2—C3177.9 (4)Br1'—C1'—C2'—C3'177.8 (4)
C1—C2—C3—C3A1.1 (6)C1'—C2'—C3'—C3A'0.7 (6)
C1—C2—C3—Br2179.4 (4)C1'—C2'—C3'—Br2'179.1 (4)
C2—C3—C3A—C4177.3 (5)C2'—C3'—C3A'—C4'178.0 (5)
Br2—C3—C3A—C42.3 (8)Br2'—C3'—C3A'—C4'0.4 (8)
C2—C3—C3A—C8A0.8 (6)C2'—C3'—C3A'—C8A'0.1 (6)
Br2—C3—C3A—C8A179.6 (4)Br2'—C3'—C3A'—C8A'178.3 (4)
C3—C3A—C4—C5177.8 (5)C3'—C3A'—C4'—C5'178.0 (6)
C8A—C3A—C4—C50.1 (9)C8A'—C3A'—C4'—C5'0.5 (10)
C3A—C4—C5—C62.5 (10)C3A'—C4'—C5'—C6'1.4 (10)
C4—C5—C6—C70.4 (10)C4'—C5'—C6'—C7'1.8 (10)
C4—C5—C6—C9178.5 (5)C4'—C5'—C6'—C9'178.3 (5)
C5—C6—C7—C81.9 (10)C5'—C6'—C7'—C8'0.5 (10)
C9—C6—C7—C8179.2 (5)C9'—C6'—C7'—C8'179.6 (6)
C6—C7—C8—C8A0.3 (10)C6'—C7'—C8'—C8A'0.2 (10)
C7—C8—C8A—C1178.3 (6)C2'—C1'—C8A'—C8'179.0 (5)
C7—C8—C8A—C3A4.4 (9)Br1'—C1'—C8A'—C8'2.7 (8)
C2—C1—C8A—C8178.2 (5)C2'—C1'—C8A'—C3A'1.3 (6)
Br1—C1—C8A—C84.8 (9)Br1'—C1'—C8A'—C3A'177.7 (4)
C2—C1—C8A—C3A0.3 (6)C7'—C8'—C8A'—C1'179.7 (6)
Br1—C1—C8A—C3A177.4 (4)C7'—C8'—C8A'—C3A'0.7 (10)
C4—C3A—C8A—C84.3 (9)C4'—C3A'—C8A'—C1'178.8 (5)
C3—C3A—C8A—C8177.6 (5)C3'—C3A'—C8A'—C1'0.9 (6)
C4—C3A—C8A—C1177.8 (5)C4'—C3A'—C8A'—C8'1.6 (9)
C3—C3A—C8A—C10.3 (6)C3'—C3A'—C8A'—C8'179.5 (5)
C10—O1—C9—O21.1 (8)C10'—O1'—C9'—O2'0.8 (8)
C10—O1—C9—C6177.4 (4)C10'—O1'—C9'—C6'179.2 (4)
C7—C6—C9—O24.5 (8)C7'—C6'—C9'—O2'3.9 (8)
C5—C6—C9—O2174.5 (5)C5'—C6'—C9'—O2'176.2 (5)
C7—C6—C9—O1177.0 (5)C7'—C6'—C9'—O1'176.0 (5)
C5—C6—C9—O14.0 (7)C5'—C6'—C9'—O1'3.8 (7)
C9—O1—C10—C11170.6 (5)C9'—O1'—C10'—C11'169.9 (5)
 

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