3,5-Dibromo­salicyl alcohol hemihydrate

The asymmetric unit of the title compound, C₇H₆Br₂O₂·0.5H₂O, contains two independent 3,5-dibromo­salicyl alcohol mol­ecules and one water mol­ecule. The salicyl alcohol mol­ecules inter­act with each other and with the water mol­ecule through O—H...O hydrogen bonding, giving rise to a layer structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.041
• wR factor = 0.117
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Ra
              O3   -H3O     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.85(6), Rep   0.850(10) ......       6.00 su-Ra
              O4   -H4O     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Ra
              O1W  -H1W1    1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(6), Rep   0.850(10) ......       6.00 su-Ra
              O4   -H4O     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Ra
              O1W  -H1#     1.555   1.555

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.67
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O2   -H2O     1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      110(5), Rep      110(2) ......       2.50 su-Ra
              H1W1 -O1W  -H1W2    1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O2   -H2O     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.99(5), Rep     1.99(2) ......       2.50 su-Ra
              H2O  -O4      1.555   1.445
PLAT736_ALERT_1_C H...A   Calc     2.05(5), Rep     2.05(2) ......       2.50 su-Ra
              H1#  -O2      1.555   1.565
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C7 H6 Br2 O2

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.672
            Tmax scaled      0.197 Tmin scaled      0.066
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

  16 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
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

3,5-Dibromosalicyl alcohol hemihydrate

Crystal data

C7H6Br2O2·0.5H2O	Z = 4
Mr = 290.95	F(000) = 556
Triclinic, P1	Dx = 2.159 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.034 (1) Å	Cell parameters from 1304 reflections
b = 8.484 (1) Å	θ = 2.6–23.8°
c = 15.569 (2) Å	µ = 9.01 mm^−1
α = 99.682 (2)°	T = 293 K
β = 91.695 (2)°	Block, colourless
γ = 101.661 (2)°	0.48 × 0.20 × 0.18 mm
V = 895.0 (2) Å^3

Data collection

Bruker APEX2 area-detector diffractometer	3107 independent reflections
Radiation source: fine-focus sealed tube	2351 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.098, Tmax = 0.294	k = −6→10
4711 measured reflections	l = −18→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0641P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3107 reflections	Δρmax = 0.65 e Å^−3
227 parameters	Δρmin = −0.49 e Å^−3
7 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (2)

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

	x	y	z	Uiso*/Ueq
Br1	0.6611 (1)	0.41254 (7)	0.81082 (4)	0.0434 (2)
Br2	0.5602 (1)	−0.19982 (8)	0.91991 (4)	0.0504 (3)
Br3	1.1618 (1)	1.38258 (9)	0.93414 (5)	0.0574 (3)
Br4	1.0807 (1)	1.26687 (9)	0.56465 (5)	0.0536 (3)
O1	0.5620 (7)	0.1806 (5)	0.6281 (3)	0.041 (1)
O2	0.3696 (6)	−0.3209 (5)	0.5769 (3)	0.036 (1)
O3	1.0822 (7)	1.0034 (5)	0.9004 (3)	0.049 (1)
O4	1.0243 (7)	0.6838 (5)	0.6649 (3)	0.05 (1)
O1w	0.6667 (6)	0.4982 (5)	0.5939 (3)	0.041 (1)
C1	0.4562 (9)	−0.1492 (7)	0.5841 (4)	0.035 (1)
C2	0.5110 (8)	−0.0682 (6)	0.6780 (4)	0.027 (1)
C3	0.5618 (7)	0.1041 (7)	0.6966 (4)	0.028 (1)
C4	0.6051 (7)	0.1804 (6)	0.7837 (4)	0.028 (1)
C5	0.6068 (8)	0.0946 (7)	0.8501 (4)	0.033 (1)
C6	0.5595 (8)	−0.0747 (7)	0.8301 (4)	0.029 (1)
C7	0.5119 (8)	−0.1546 (7)	0.7446 (4)	0.030 (1)
C8	1.0129 (10)	0.7777 (7)	0.7475 (5)	0.043 (2)
C9	1.0485 (8)	0.9594 (7)	0.7469 (4)	0.031 (1)
C10	1.0856 (8)	1.0679 (7)	0.8263 (4)	0.034 (1)
C11	1.1191 (8)	1.2353 (7)	0.8256 (4)	0.036 (2)
C12	1.1205 (8)	1.2969 (7)	0.7484 (4)	0.036 (2)
C13	1.0811 (9)	1.1855 (8)	0.6706 (4)	0.038 (2)
C14	1.0455 (8)	1.0188 (7)	0.6697 (4)	0.039 (1)
H1o	0.561 (9)	0.281 (2)	0.635 (4)	0.049*
H2o	0.259 (5)	−0.329 (8)	0.598 (4)	0.055*
H3o	1.125 (10)	1.087 (5)	0.939 (3)	0.059*
H4o	0.935 (7)	0.613 (7)	0.634 (4)	0.065*
H1w1	0.568 (6)	0.542 (7)	0.600 (3)	0.050*
H1w2	0.673 (8)	0.458 (7)	0.541 (1)	0.050*
H1a	0.3650	−0.0950	0.5590	0.042*
H1b	0.5716	−0.1373	0.5511	0.042*
H5	0.6389	0.1483	0.9074	0.039*
H7	0.4802	−0.2683	0.7324	0.035*
H8a	1.1080	0.7572	0.7883	0.052*
H8b	0.8850	0.7427	0.7680	0.052*
H12	1.1468	1.4089	0.7488	0.043*
H14	1.0195	0.9463	0.6168	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0611 (5)	0.0237 (3)	0.0427 (4)	0.0072 (3)	−0.0020 (3)	0.0014 (3)
Br2	0.0878 (6)	0.0369 (4)	0.0296 (4)	0.0151 (3)	0.0021 (3)	0.0124 (3)
Br3	0.0863 (6)	0.0422 (4)	0.0388 (4)	0.0154 (4)	−0.0041 (4)	−0.0072 (3)
Br4	0.0719 (5)	0.0543 (5)	0.0397 (4)	0.0205 (4)	0.0033 (4)	0.0140 (3)
O1	0.065 (3)	0.028 (2)	0.033 (3)	0.009 (2)	0.003 (2)	0.012 (2)
O2	0.043 (3)	0.029 (2)	0.033 (2)	0.0047 (19)	0.001 (2)	−0.0010 (18)
O3	0.064 (3)	0.040 (3)	0.042 (3)	0.006 (2)	0.001 (2)	0.011 (2)
O4	0.057 (3)	0.035 (3)	0.059 (3)	0.003 (2)	0.002 (3)	−0.012 (2)
O1w	0.053 (3)	0.040 (3)	0.032 (2)	0.013 (2)	−0.002 (2)	0.005 (2)
C1	0.043 (4)	0.036 (3)	0.028 (3)	0.012 (3)	−0.003 (3)	0.006 (3)
C2	0.029 (3)	0.027 (3)	0.023 (3)	0.007 (2)	−0.001 (2)	0.002 (2)
C3	0.026 (3)	0.026 (3)	0.033 (3)	0.008 (2)	0.003 (2)	0.009 (3)
C4	0.028 (3)	0.021 (3)	0.032 (3)	0.005 (2)	−0.001 (2)	0.000 (2)
C5	0.044 (4)	0.030 (3)	0.024 (3)	0.010 (3)	0.002 (3)	0.001 (3)
C6	0.040 (3)	0.027 (3)	0.026 (3)	0.013 (2)	0.000 (3)	0.012 (2)
C7	0.037 (3)	0.024 (3)	0.029 (3)	0.011 (2)	0.001 (3)	0.003 (2)
C8	0.043 (4)	0.034 (4)	0.050 (4)	0.004 (3)	0.002 (3)	0.003 (3)
C9	0.024 (3)	0.032 (3)	0.038 (4)	0.007 (2)	0.006 (3)	0.005 (3)
C10	0.030 (3)	0.035 (3)	0.036 (4)	0.006 (3)	0.002 (3)	0.008 (3)
C11	0.036 (3)	0.028 (3)	0.039 (4)	0.008 (3)	0.000 (3)	−0.007 (3)
C12	0.042 (4)	0.025 (3)	0.044 (4)	0.011 (3)	−0.002 (3)	0.010 (3)
C13	0.037 (3)	0.043 (4)	0.035 (4)	0.011 (3)	0.001 (3)	0.010 (3)
C14	0.036 (3)	0.035 (4)	0.041 (4)	0.007 (3)	0.003 (3)	−0.004 (3)

Geometric parameters (Å, º)

Br1—C4	1.900 (5)	C10—C11	1.394 (8)
Br2—C6	1.893 (5)	C11—C12	1.389 (8)
Br3—C11	1.902 (6)	C12—C13	1.387 (8)
Br4—C13	1.893 (6)	C13—C14	1.384 (8)
O1—C3	1.339 (7)	O1—H1o	0.85 (1)
O2—C1	1.444 (7)	O2—H2o	0.85 (1)
O3—C10	1.355 (7)	O3—H3o	0.85 (1)
O4—C8	1.408 (8)	O4—H4o	0.85 (1)
C1—C2	1.510 (7)	O1w—H1w1	0.85 (1)
C2—C7	1.368 (8)	O1w—H1w2	0.85 (1)
C2—C3	1.410 (7)	C1—H1a	0.97
C3—C4	1.396 (8)	C1—H1a	0.97
C4—C5	1.362 (8)	C5—H5	0.93
C5—C6	1.386 (7)	C7—H7	0.93
C6—C7	1.387 (8)	C8—H8a	0.97
C8—C9	1.513 (8)	C8—H8b	0.97
C9—C14	1.379 (9)	C12—H12	0.93
C9—C10	1.395 (8)	C14—H14	0.93
C3—O1—H1o	121 (5)	C12—C11—Br3	119.4 (4)
C1—O2—H2o	108 (5)	C10—C11—Br3	118.6 (5)
C10—O3—H3o	102 (5)	C13—C12—C11	117.7 (5)
C8—O4—H4o	128 (5)	C14—C13—C12	121.3 (6)
O2—C1—C2	111.6 (5)	C14—C13—Br4	120.3 (5)
C7—C2—C3	119.4 (5)	C12—C13—Br4	118.4 (5)
C7—C2—C1	122.8 (5)	C9—C14—C13	120.3 (6)
C3—C2—C1	117.8 (5)	H1w1—O1w—H1w2	110 (2)
O1—C3—C4	125.6 (5)	O2—C1—H1a	109.3
O1—C3—C2	116.2 (5)	C2—C1—H1a	109.3
C4—C3—C2	118.2 (5)	O2—C1—H1b	109.3
C5—C4—C3	122.5 (5)	C2—C1—H1b	109.3
C5—C4—Br1	118.7 (4)	H1a—C1—H1b	108.0
C3—C4—Br1	118.9 (4)	C4—C5—H5	120.8
C4—C5—C6	118.4 (5)	C6—C5—H5	120.8
C5—C6—C7	120.8 (5)	C2—C7—H7	119.6
C5—C6—Br2	120.1 (4)	C6—C7—H7	119.6
C7—C6—Br2	119.1 (4)	O4—C8—H8a	108.9
C2—C7—C6	120.7 (5)	C9—C8—H8a	108.9
O4—C8—C9	113.2 (5)	O4—C8—H8b	108.9
C14—C9—C10	119.9 (5)	C9—C8—H8b	108.9
C14—C9—C8	121.3 (5)	H8a—C8—H8b	107.8
C10—C9—C8	118.8 (6)	C13—C12—H12	121.1
O3—C10—C9	117.6 (5)	C11—C12—H12	121.1
O3—C10—C11	123.7 (5)	C9—C14—H14	119.8
C9—C10—C11	118.7 (6)	C13—C14—H14	119.8
C12—C11—C10	122.0 (5)
O2—C1—C2—C7	11.6 (8)	O4—C8—C9—C14	14.3 (8)
O2—C1—C2—C3	−168.0 (5)	O4—C8—C9—C10	−165.5 (5)
C7—C2—C3—O1	178.6 (5)	C14—C9—C10—O3	178.4 (5)
C1—C2—C3—O1	−1.8 (7)	C8—C9—C10—O3	−1.8 (8)
C7—C2—C3—C4	−2.2 (8)	C14—C9—C10—C11	0.0 (8)
C1—C2—C3—C4	177.5 (5)	C8—C9—C10—C11	179.8 (5)
O1—C3—C4—C5	−178.3 (5)	O3—C10—C11—C12	−179.6 (5)
C2—C3—C4—C5	2.5 (8)	C9—C10—C11—C12	−1.4 (9)
O1—C3—C4—Br1	2.4 (8)	O3—C10—C11—Br3	−0.2 (8)
C2—C3—C4—Br1	−176.8 (4)	C9—C10—C11—Br3	178.1 (4)
C3—C4—C5—C6	−1.4 (9)	C10—C11—C12—C13	2.0 (9)
Br1—C4—C5—C6	177.9 (4)	Br3—C11—C12—C13	−177.5 (4)
C4—C5—C6—C7	0.1 (9)	C11—C12—C13—C14	−1.3 (9)
C4—C5—C6—Br2	179.8 (4)	C11—C12—C13—Br4	179.6 (4)
C3—C2—C7—C6	0.9 (8)	C10—C9—C14—C13	0.7 (9)
C1—C2—C7—C6	−178.7 (5)	C8—C9—C14—C13	−179.1 (5)
C5—C6—C7—C2	0.1 (9)	C12—C13—C14—C9	0.0 (9)
Br2—C6—C7—C2	−179.6 (4)	Br4—C13—C14—C9	179.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O1w	0.85 (1)	2.05 (4)	2.791 (6)	146 (6)
O2—H2o···O4^i	0.85 (1)	1.99 (2)	2.828 (6)	169 (7)
O4—H4o···O1w	0.85 (1)	1.97 (3)	2.771 (6)	157 (7)
O1w—H1w1···O2^ii	0.85 (1)	2.05 (2)	2.862 (6)	160 (6)
O1w—H1w2···O2^iii	0.85 (1)	1.98 (2)	2.803 (6)	165 (6)

Symmetry codes: (i) x−1, y−1, z; (ii) x, y+1, z; (iii) −x+1, −y, −z+1.