Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017278/pr2002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017278/pr2002Isup2.hkl |
CCDC reference: 647297
Key indicators
- Single-crystal X-ray study
- T = 100 K
- R factor = 0.027
- wR factor = 0.077
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level B Crystal system given = monoclinic PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 80 PerFi PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... m PLAT480_ALERT_4_B Long H...A H-Bond Reported H12 .. BR1 .. 3.37 Ang.
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.430 From the CIF: _refine_ls_abs_structure_Flack_su 0.030 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.43 PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. N1 .. 3.38 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. BR1 .. 3.17 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. BR1 .. 3.10 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. N1 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. N1 .. 2.71 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C7 H4 Br N O
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 27.17 From the CIF: _reflns_number_total 1428 Count of symmetry unique reflns 767 Completeness (_total/calc) 186.18% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 661 Fraction of Friedel pairs measured 0.862 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 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 4 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 9 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C7H4BrNO | F(000) = 192 |
Mr = 198.02 | Dx = 2.006 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8265 (2) Å | Cell parameters from 759 reflections |
b = 9.6148 (6) Å | θ = 2–27.0° |
c = 8.9964 (5) Å | µ = 6.18 mm−1 |
β = 97.948 (4)° | T = 100 K |
V = 327.81 (3) Å3 | Needle, colourless |
Z = 2 | 0.5 × 0.05 × 0.05 mm |
Enraf–Nonius KappaCCD diffractometer | 1428 independent reflections |
Radiation source: Enraf–Nonius FR590 | 1341 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 9 pixels mm-1 | θmax = 27.2°, θmin = 2.3° |
CCD rotation images, thick slices scans | h = −4→4 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004; Blessing, 1995) | k = −12→12 |
Tmin = 0.335, Tmax = 0.734 | l = −11→11 |
4797 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0267P)2 + 0.9024P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
1428 reflections | Δρmax = 0.72 e Å−3 |
96 parameters | Δρmin = −0.54 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.43 (3) |
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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
Br1 | −0.44854 (8) | 0.49338 (13) | −0.13265 (3) | 0.01714 (11) | |
O1 | 0.3479 (8) | 0.3514 (3) | 0.5159 (3) | 0.0217 (7) | |
N1 | 0.3408 (8) | 0.4967 (9) | 0.4895 (3) | 0.0190 (6) | |
C10 | −0.2150 (8) | 0.4917 (11) | 0.0681 (3) | 0.0142 (6) | |
C11 | −0.111 (2) | 0.6253 (8) | 0.1338 (7) | 0.0157 (16) | |
H11 | −0.1759 | 0.7080 | 0.0790 | 0.019* | |
C12 | 0.078 (2) | 0.6341 (7) | 0.2730 (9) | 0.0174 (13) | |
H12 | 0.1539 | 0.7211 | 0.3159 | 0.021* | |
C13 | 0.1594 (10) | 0.5045 (12) | 0.3530 (4) | 0.0204 (11) | |
C14 | 0.0442 (19) | 0.3776 (6) | 0.2887 (8) | 0.0154 (15) | |
C15 | −0.147 (2) | 0.3704 (8) | 0.1408 (8) | 0.0164 (15) | |
H15 | −0.2228 | 0.2841 | 0.0960 | 0.020* | |
C16 | 0.1740 (13) | 0.2835 (5) | 0.3965 (5) | 0.0209 (9) | |
H16 | 0.151 (12) | 0.182 (5) | 0.405 (5) | 0.017 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01588 (17) | 0.02112 (17) | 0.01345 (15) | 0.0000 (4) | −0.00143 (11) | −0.0004 (5) |
O1 | 0.0267 (18) | 0.0208 (15) | 0.0169 (15) | 0.0012 (13) | 0.0003 (13) | 0.0036 (12) |
N1 | 0.0227 (15) | 0.0163 (14) | 0.0173 (13) | 0.001 (4) | −0.0002 (10) | 0.002 (4) |
C10 | 0.0104 (14) | 0.0185 (15) | 0.0138 (14) | −0.003 (4) | 0.0017 (11) | −0.007 (5) |
C11 | 0.017 (3) | 0.010 (3) | 0.020 (3) | 0.001 (2) | 0.001 (3) | −0.001 (2) |
C12 | 0.015 (3) | 0.014 (2) | 0.024 (3) | 0.001 (2) | 0.006 (2) | −0.003 (2) |
C13 | 0.0170 (17) | 0.031 (3) | 0.0138 (15) | −0.001 (3) | 0.0052 (13) | −0.006 (3) |
C14 | 0.011 (3) | 0.022 (3) | 0.012 (3) | 0.000 (2) | 0.000 (2) | 0.004 (2) |
C15 | 0.018 (3) | 0.019 (4) | 0.012 (3) | −0.003 (3) | 0.002 (2) | −0.004 (2) |
C16 | 0.028 (3) | 0.019 (2) | 0.016 (2) | 0.0030 (18) | 0.0042 (18) | 0.0007 (16) |
Br1—C10 | 1.901 (3) | C12—C13 | 1.451 (13) |
O1—C16 | 1.351 (6) | C12—H12 | 0.9500 |
O1—N1 | 1.417 (9) | C13—C14 | 1.395 (13) |
N1—C13 | 1.326 (5) | C14—C16 | 1.368 (8) |
C10—C15 | 1.345 (12) | C14—C15 | 1.429 (10) |
C10—C11 | 1.447 (12) | C15—H15 | 0.9500 |
C11—C12 | 1.360 (10) | C16—H16 | 0.98 (5) |
C11—H11 | 0.9500 | ||
C16—O1—N1 | 110.3 (3) | N1—C13—C12 | 123.8 (9) |
C13—N1—O1 | 101.9 (7) | C14—C13—C12 | 120.8 (3) |
C15—C10—C11 | 123.2 (3) | C16—C14—C13 | 102.8 (6) |
C15—C10—Br1 | 120.2 (6) | C16—C14—C15 | 135.8 (7) |
C11—C10—Br1 | 116.6 (6) | C13—C14—C15 | 121.4 (7) |
C12—C11—C10 | 120.8 (7) | C10—C15—C14 | 116.8 (7) |
C12—C11—H11 | 119.6 | C10—C15—H15 | 121.6 |
C10—C11—H11 | 119.6 | C14—C15—H15 | 121.6 |
C11—C12—C13 | 117.0 (7) | O1—C16—C14 | 109.5 (4) |
C11—C12—H12 | 121.5 | O1—C16—H16 | 117 (3) |
C13—C12—H12 | 121.5 | C14—C16—H16 | 133 (3) |
N1—C13—C14 | 115.5 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···Br1i | 0.95 | 3.17 | 3.919 (8) | 138 |
C12—H12···Br1ii | 0.95 | 3.37 | 4.004 (7) | 126 |
C12—H12···O1iii | 0.95 | 2.59 | 3.412 (8) | 145 |
C15—H15···Br1iv | 0.95 | 3.10 | 3.938 (8) | 148 |
C16—H16···N1v | 0.98 (5) | 2.85 (5) | 3.618 (8) | 136 (3) |
C16—H16···N1vi | 0.98 (5) | 2.71 (5) | 3.402 (8) | 128 (4) |
Symmetry codes: (i) −x−1, y+1/2, −z; (ii) −x, y+1/2, −z; (iii) −x+1, y+1/2, −z+1; (iv) −x−1, y−1/2, −z; (v) −x, y−1/2, −z+1; (vi) −x+1, y−1/2, −z+1. |
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