Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601453X/ob2012sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601453X/ob2012Isup2.hkl |
CCDC reference: 608466
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.044
- wR factor = 0.119
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _diffrn_reflns_theta_full 25.01 From the CIF: _reflns_number_total 3346 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3670 Completeness (_total/calc) 91.17% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.34 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C25 H22 Br N O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C25H22BrNO | F(000) = 444 |
Mr = 432.35 | Dx = 1.385 Mg m−3 |
Triclinic, P1 | Melting point > 573 K |
a = 7.296 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.597 (5) Å | Cell parameters from 1419 reflections |
c = 15.304 (8) Å | θ = 2.2–21.5° |
α = 94.038 (7)° | µ = 2.00 mm−1 |
β = 93.465 (8)° | T = 298 K |
γ = 103.331 (7)° | Block, colourless |
V = 1036.9 (9) Å3 | 0.32 × 0.27 × 0.09 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 3346 independent reflections |
Radiation source: fine-focus sealed tube | 2053 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→8 |
Tmin = 0.567, Tmax = 0.841 | k = −11→11 |
5522 measured reflections | l = −17→18 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.7039P] where P = (Fo2 + 2Fc2)/3 |
3346 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
Experimental. IR (Medium?, ν, cm-1): 3264, 1595, 1520, 1493 |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.93962 (8) | 1.74848 (7) | 1.07677 (3) | 0.1010 (3) | |
N1 | 0.2911 (4) | 1.3099 (3) | 0.69343 (18) | 0.0449 (8) | |
H1 | 0.1747 | 1.2831 | 0.7046 | 0.054* | |
O1 | 0.8973 (4) | 1.2255 (3) | 0.71271 (18) | 0.0580 (7) | |
C1 | 0.4123 (5) | 1.2283 (4) | 0.7162 (2) | 0.0396 (8) | |
C2 | 0.3258 (5) | 1.0790 (4) | 0.7376 (2) | 0.0478 (9) | |
H2A | 0.2819 | 1.0190 | 0.6833 | 0.057* | |
H2B | 0.2168 | 1.0805 | 0.7706 | 0.057* | |
C3 | 0.4625 (5) | 1.0127 (4) | 0.7906 (3) | 0.0519 (10) | |
C4 | 0.6466 (5) | 1.0348 (4) | 0.7445 (3) | 0.0521 (10) | |
H4A | 0.7401 | 1.0042 | 0.7814 | 0.063* | |
H4B | 0.6236 | 0.9730 | 0.6900 | 0.063* | |
C5 | 0.7273 (5) | 1.1860 (4) | 0.7239 (2) | 0.0413 (9) | |
C6 | 0.6023 (5) | 1.2813 (3) | 0.7154 (2) | 0.0366 (8) | |
C7 | 0.6818 (5) | 1.4388 (4) | 0.7054 (2) | 0.0390 (8) | |
H7 | 0.7930 | 1.4466 | 0.6715 | 0.047* | |
C8 | 0.5404 (5) | 1.5017 (4) | 0.6545 (2) | 0.0387 (8) | |
C9 | 0.5975 (5) | 1.6276 (4) | 0.6087 (2) | 0.0424 (9) | |
C10 | 0.7891 (6) | 1.7034 (4) | 0.6103 (2) | 0.0528 (10) | |
H10 | 0.8814 | 1.6719 | 0.6426 | 0.063* | |
C11 | 0.8399 (7) | 1.8218 (4) | 0.5649 (3) | 0.0652 (12) | |
H11 | 0.9665 | 1.8698 | 0.5665 | 0.078* | |
C12 | 0.7044 (8) | 1.8718 (5) | 0.5163 (3) | 0.0721 (14) | |
H12 | 0.7412 | 1.9519 | 0.4850 | 0.087* | |
C13 | 0.5193 (7) | 1.8043 (5) | 0.5145 (3) | 0.0640 (12) | |
H13 | 0.4300 | 1.8392 | 0.4822 | 0.077* | |
C14 | 0.4600 (6) | 1.6817 (4) | 0.5609 (2) | 0.0489 (10) | |
C15 | 0.2685 (6) | 1.6096 (4) | 0.5611 (2) | 0.0549 (11) | |
H15 | 0.1772 | 1.6437 | 0.5297 | 0.066* | |
C16 | 0.2139 (5) | 1.4923 (4) | 0.6057 (2) | 0.0503 (10) | |
H16 | 0.0864 | 1.4480 | 0.6059 | 0.060* | |
C17 | 0.3504 (5) | 1.4371 (4) | 0.6521 (2) | 0.0398 (8) | |
C18 | 0.3754 (7) | 0.8520 (5) | 0.7935 (4) | 0.0877 (16) | |
H18A | 0.3505 | 0.8065 | 0.7347 | 0.132* | |
H18B | 0.2594 | 0.8394 | 0.8217 | 0.132* | |
H18C | 0.4618 | 0.8093 | 0.8259 | 0.132* | |
C19 | 0.5008 (6) | 1.0841 (5) | 0.8847 (3) | 0.0707 (13) | |
H19A | 0.5863 | 1.0407 | 0.9173 | 0.106* | |
H19B | 0.3842 | 1.0714 | 0.9124 | 0.106* | |
H19C | 0.5560 | 1.1849 | 0.8835 | 0.106* | |
C20 | 0.7469 (5) | 1.5202 (4) | 0.7953 (2) | 0.0400 (8) | |
C21 | 0.9341 (5) | 1.5594 (4) | 0.8255 (3) | 0.0581 (11) | |
H21 | 1.0243 | 1.5399 | 0.7891 | 0.070* | |
C22 | 0.9920 (6) | 1.6271 (5) | 0.9086 (3) | 0.0701 (12) | |
H22 | 1.1195 | 1.6517 | 0.9281 | 0.084* | |
C23 | 0.8606 (6) | 1.6574 (4) | 0.9617 (3) | 0.0580 (11) | |
C24 | 0.6729 (6) | 1.6199 (5) | 0.9345 (3) | 0.0652 (12) | |
H24 | 0.5837 | 1.6406 | 0.9710 | 0.078* | |
C25 | 0.6177 (6) | 1.5507 (4) | 0.8517 (3) | 0.0572 (11) | |
H25 | 0.4896 | 1.5237 | 0.8333 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1031 (5) | 0.1231 (5) | 0.0694 (3) | 0.0323 (4) | −0.0238 (3) | −0.0347 (3) |
N1 | 0.0261 (17) | 0.059 (2) | 0.0488 (18) | 0.0062 (15) | 0.0059 (14) | 0.0107 (15) |
O1 | 0.0340 (16) | 0.0626 (18) | 0.0800 (19) | 0.0147 (13) | 0.0102 (14) | 0.0094 (14) |
C1 | 0.035 (2) | 0.048 (2) | 0.0352 (18) | 0.0093 (18) | 0.0024 (16) | 0.0074 (15) |
C2 | 0.038 (2) | 0.053 (2) | 0.047 (2) | −0.0004 (18) | 0.0057 (17) | 0.0038 (17) |
C3 | 0.052 (3) | 0.044 (2) | 0.058 (2) | 0.0046 (19) | 0.011 (2) | 0.0121 (18) |
C4 | 0.052 (3) | 0.047 (2) | 0.060 (2) | 0.0167 (19) | 0.006 (2) | 0.0057 (18) |
C5 | 0.037 (2) | 0.048 (2) | 0.0379 (19) | 0.0098 (18) | 0.0031 (17) | −0.0013 (16) |
C6 | 0.030 (2) | 0.040 (2) | 0.0381 (18) | 0.0047 (16) | 0.0038 (15) | 0.0049 (15) |
C7 | 0.027 (2) | 0.046 (2) | 0.045 (2) | 0.0066 (16) | 0.0064 (16) | 0.0087 (16) |
C8 | 0.033 (2) | 0.044 (2) | 0.0394 (19) | 0.0110 (17) | 0.0034 (16) | 0.0042 (16) |
C9 | 0.047 (3) | 0.045 (2) | 0.0372 (19) | 0.0136 (18) | 0.0090 (17) | 0.0052 (16) |
C10 | 0.051 (3) | 0.050 (2) | 0.057 (2) | 0.0080 (19) | 0.013 (2) | 0.0106 (19) |
C11 | 0.074 (3) | 0.053 (3) | 0.069 (3) | 0.008 (2) | 0.024 (2) | 0.015 (2) |
C12 | 0.108 (4) | 0.055 (3) | 0.058 (3) | 0.020 (3) | 0.023 (3) | 0.019 (2) |
C13 | 0.094 (4) | 0.060 (3) | 0.045 (2) | 0.031 (3) | 0.004 (2) | 0.013 (2) |
C14 | 0.062 (3) | 0.051 (2) | 0.038 (2) | 0.022 (2) | 0.0032 (19) | 0.0044 (17) |
C15 | 0.061 (3) | 0.065 (3) | 0.044 (2) | 0.032 (2) | −0.008 (2) | 0.003 (2) |
C16 | 0.040 (2) | 0.067 (3) | 0.047 (2) | 0.021 (2) | −0.0008 (18) | 0.003 (2) |
C17 | 0.035 (2) | 0.051 (2) | 0.0357 (18) | 0.0145 (18) | 0.0046 (16) | 0.0035 (16) |
C18 | 0.083 (4) | 0.055 (3) | 0.125 (4) | 0.008 (3) | 0.024 (3) | 0.026 (3) |
C19 | 0.069 (3) | 0.096 (4) | 0.052 (3) | 0.022 (3) | 0.011 (2) | 0.023 (2) |
C20 | 0.035 (2) | 0.038 (2) | 0.045 (2) | 0.0029 (16) | −0.0010 (17) | 0.0070 (15) |
C21 | 0.033 (3) | 0.079 (3) | 0.056 (2) | 0.003 (2) | 0.004 (2) | 0.001 (2) |
C22 | 0.042 (3) | 0.091 (3) | 0.066 (3) | −0.002 (2) | −0.008 (2) | −0.006 (2) |
C23 | 0.058 (3) | 0.061 (3) | 0.050 (2) | 0.011 (2) | −0.010 (2) | −0.0044 (19) |
C24 | 0.063 (3) | 0.078 (3) | 0.057 (3) | 0.027 (2) | 0.003 (2) | −0.007 (2) |
C25 | 0.042 (3) | 0.070 (3) | 0.059 (2) | 0.015 (2) | −0.002 (2) | −0.009 (2) |
Br1—C23 | 1.904 (4) | C11—C12 | 1.394 (6) |
N1—C1 | 1.356 (4) | C11—H11 | 0.9300 |
N1—C17 | 1.405 (4) | C12—C13 | 1.354 (6) |
N1—H1 | 0.8600 | C12—H12 | 0.9300 |
O1—C5 | 1.237 (4) | C13—C14 | 1.414 (5) |
C1—C6 | 1.363 (4) | C13—H13 | 0.9300 |
C1—C2 | 1.493 (5) | C14—C15 | 1.409 (5) |
C2—C3 | 1.525 (5) | C15—C16 | 1.352 (5) |
C2—H2A | 0.9700 | C15—H15 | 0.9300 |
C2—H2B | 0.9700 | C16—C17 | 1.409 (5) |
C3—C19 | 1.531 (5) | C16—H16 | 0.9300 |
C3—C18 | 1.532 (5) | C18—H18A | 0.9600 |
C3—C4 | 1.534 (5) | C18—H18B | 0.9600 |
C4—C5 | 1.498 (5) | C18—H18C | 0.9600 |
C4—H4A | 0.9700 | C19—H19A | 0.9600 |
C4—H4B | 0.9700 | C19—H19B | 0.9600 |
C5—C6 | 1.439 (5) | C19—H19C | 0.9600 |
C6—C7 | 1.512 (5) | C20—C21 | 1.372 (5) |
C7—C8 | 1.513 (5) | C20—C25 | 1.382 (5) |
C7—C20 | 1.526 (5) | C21—C22 | 1.382 (5) |
C7—H7 | 0.9800 | C21—H21 | 0.9300 |
C8—C17 | 1.379 (5) | C22—C23 | 1.361 (6) |
C8—C9 | 1.431 (5) | C22—H22 | 0.9300 |
C9—C10 | 1.417 (5) | C23—C24 | 1.365 (6) |
C9—C14 | 1.420 (5) | C24—C25 | 1.380 (5) |
C10—C11 | 1.363 (5) | C24—H24 | 0.9300 |
C10—H10 | 0.9300 | C25—H25 | 0.9300 |
C1—N1—C17 | 121.9 (3) | C13—C12—C11 | 120.3 (4) |
C1—N1—H1 | 119.1 | C13—C12—H12 | 119.9 |
C17—N1—H1 | 119.1 | C11—C12—H12 | 119.9 |
N1—C1—C6 | 120.1 (3) | C12—C13—C14 | 120.9 (4) |
N1—C1—C2 | 116.6 (3) | C12—C13—H13 | 119.6 |
C6—C1—C2 | 123.3 (3) | C14—C13—H13 | 119.6 |
C1—C2—C3 | 113.0 (3) | C15—C14—C13 | 122.4 (4) |
C1—C2—H2A | 109.0 | C15—C14—C9 | 118.4 (3) |
C3—C2—H2A | 109.0 | C13—C14—C9 | 119.2 (4) |
C1—C2—H2B | 109.0 | C16—C15—C14 | 121.7 (4) |
C3—C2—H2B | 109.0 | C16—C15—H15 | 119.1 |
H2A—C2—H2B | 107.8 | C14—C15—H15 | 119.1 |
C2—C3—C19 | 110.6 (3) | C15—C16—C17 | 120.0 (4) |
C2—C3—C18 | 109.1 (3) | C15—C16—H16 | 120.0 |
C19—C3—C18 | 109.0 (3) | C17—C16—H16 | 120.0 |
C2—C3—C4 | 107.7 (3) | C8—C17—N1 | 119.6 (3) |
C19—C3—C4 | 110.3 (3) | C8—C17—C16 | 121.4 (3) |
C18—C3—C4 | 110.2 (3) | N1—C17—C16 | 118.9 (3) |
C5—C4—C3 | 115.0 (3) | C3—C18—H18A | 109.5 |
C5—C4—H4A | 108.5 | C3—C18—H18B | 109.5 |
C3—C4—H4A | 108.5 | H18A—C18—H18B | 109.5 |
C5—C4—H4B | 108.5 | C3—C18—H18C | 109.5 |
C3—C4—H4B | 108.5 | H18A—C18—H18C | 109.5 |
H4A—C4—H4B | 107.5 | H18B—C18—H18C | 109.5 |
O1—C5—C6 | 121.5 (3) | C3—C19—H19A | 109.5 |
O1—C5—C4 | 119.9 (3) | C3—C19—H19B | 109.5 |
C6—C5—C4 | 118.6 (3) | H19A—C19—H19B | 109.5 |
C1—C6—C5 | 119.5 (3) | C3—C19—H19C | 109.5 |
C1—C6—C7 | 120.4 (3) | H19A—C19—H19C | 109.5 |
C5—C6—C7 | 120.0 (3) | H19B—C19—H19C | 109.5 |
C6—C7—C8 | 111.0 (3) | C21—C20—C25 | 117.2 (3) |
C6—C7—C20 | 110.1 (3) | C21—C20—C7 | 121.8 (3) |
C8—C7—C20 | 112.3 (3) | C25—C20—C7 | 121.0 (3) |
C6—C7—H7 | 107.8 | C20—C21—C22 | 121.7 (4) |
C8—C7—H7 | 107.8 | C20—C21—H21 | 119.1 |
C20—C7—H7 | 107.8 | C22—C21—H21 | 119.1 |
C17—C8—C9 | 118.5 (3) | C23—C22—C21 | 119.4 (4) |
C17—C8—C7 | 119.6 (3) | C23—C22—H22 | 120.3 |
C9—C8—C7 | 121.9 (3) | C21—C22—H22 | 120.3 |
C10—C9—C14 | 117.9 (3) | C22—C23—C24 | 120.9 (4) |
C10—C9—C8 | 122.1 (3) | C22—C23—Br1 | 119.5 (3) |
C14—C9—C8 | 120.0 (3) | C24—C23—Br1 | 119.6 (3) |
C11—C10—C9 | 120.9 (4) | C23—C24—C25 | 118.9 (4) |
C11—C10—H10 | 119.6 | C23—C24—H24 | 120.5 |
C9—C10—H10 | 119.6 | C25—C24—H24 | 120.5 |
C10—C11—C12 | 120.8 (4) | C24—C25—C20 | 122.0 (4) |
C10—C11—H11 | 119.6 | C24—C25—H25 | 119.0 |
C12—C11—H11 | 119.6 | C20—C25—H25 | 119.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 1.99 | 2.840 (4) | 172 |
Symmetry code: (i) x−1, y, z. |
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