Download citation
Download citation
link to html
The existing crystal structure of phenol hemihydrate is shown to be incorrect and a new model, refined from high-resolution neutron powder diffraction data, is reported.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020007719/wm5564sup1.cif
Contains datablocks PHENOL_HEMI_280K_publ, PHENOL_HEMI_280K_overall, I, PHENOL_HEMI_280K_p_01, PHENOL_HEMI_280K_p_02

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989020007719/wm5564sup2.pdf
Electronic supplementary figures and tables

txt

Text file https://doi.org/10.1107/S2056989020007719/wm5564sup3.txt
DFT geometry optimizations

CCDC reference: 2008230

Key indicators

  • Single-crystal X-ray study
  • T = 280 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.000
  • wR factor = 0.000
  • Data-to-parameter ratio = 0.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A DIFF001_ALERT_1_A _diffrn_radiation_type is missing The radiation type should contain one of the following * 'Cu K\a' * 'Mo K\a' * 'Ag K\a' * neutron * synchrotron The following tests will not be performed. ABSMU_01,ABSTM_02,CRYSS_01,RADNW_01
Author Response: This item is not missing, see lines 1109 and 3355
DIFF002_ALERT_1_A  _diffrn_radiation_wavelength is missing
            Radiation wavelength (A).
            The following tests will not be performed.
            RADNW_01,REFLT_03,REFNR_01,THETM_01
Author Response: The value is not missing (see lines 1108 and 3354). The values are given as a range by virtue of the white beam used.
EXPT010_ALERT_1_A  _exptl_crystal_colour (_pd_char_colour for powder) is missing
            Crystal colour.
            The following tests will not be performed.
            CRYSC_01
Author Response: This is not missing, _pd_char_colour is reported on line 811.
DIFF003_ALERT_1_A  _diffrn_measurement_device_type is missing
            Diffractometer make and type. Replaces _diffrn_measurement_type.
Author Response: This item is not missing, see lines 1111 and 3357.
POWD001_ALERT_1_A _pd_proc_ls_prof_wR_factor (R_wp) and _refine_ls_goodness_of_fit_a
              are missing. These should be present for a powder diffraction stud
Author Response: This item is not missing, see lines 825, 1201 and 3445.
REFI010_ALERT_1_A  _refine_ls_number_parameters is missing
            Number of parameters refined.
            The following tests will not be performed
            REFNR_01
Author Response: This item is not missing, the value us given on line 819
PLAT198_ALERT_1_A Missing _diffrn_ambient_temperature   Datum ....     Please Add
Author Response: This item is not missing, see lines 1109 and 3355.

Alert level B POWD004_ALERT_1_B No 'Bragg' R factor has been given. Please supply a value for _refine_ls_R_factor_all [R(F)], refine_ls_R_Fsqd_factor [R(F^2)] or _refine_ls_R_I_factor [R(I)]. PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 --C4 . 7.7 s.u.
Author Response: Value is acceptable for a powder refinement at high homologous temperature.

Alert level C REFI015_ALERT_1_C _refine_ls_shift/su_max is missing Maximum shift/s.u. ratio after final refinement cycle. The following tests will not be performed SHFSU_01
Author Response: This item is not missing, see line 815.
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
Author Response: The crystal colour is specified on line 810.
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1       --C2       .        5.5 s.u.
Author Response: Value is acceptable for a powder refinement at high homologous temperature.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2       --C3       .        6.2 s.u.
Author Response: Value is acceptable for a powder refinement at high homologous temperature.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
Author Response: Value is expected for a powder refinement at high homologous temperature.
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........         DW Check
Author Response: Dw is a perfectly acceptable notation to indicate water deuterons.
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........         Ow Check
                    D7          OW
Author Response: Dw is a perfectly acceptable notation to indicate water deuterons.
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........         Ow Check
                    O1          OW
Author Response: Ow is a perfectly acceptable notation to indicate water oxygens.
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........         Ow Check
                    O1          D7          OW
Author Response: Ow is a perfectly acceptable notation to indicate water oxygens.

Alert level G CHEMS02_ALERT_1_G Please check that you have entered the correct _publ_requested_category classification of your compound; FI or CI or EI for inorganic; FM or CM or EM for metal-organic; FO or CO or EO for organic. From the CIF: _publ_requested_category EO From the CIF: _chemical_formula_sum:C6 D7 O1.5 PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ... 0.50 Check PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing .............. 0.00002 Ang. PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing .............. 0.00001 Ang. PLAT395_ALERT_2_G Deviating X-O-Y Angle From 120 for O1 108.1 Degree PLAT395_ALERT_2_G Deviating X-O-Y Angle From 120 for Ow1 109.5 Degree PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT981_ALERT_1_G No non-zero f" Anomalous Scattering Values Found Please Check PLAT986_ALERT_1_G No non-zero f' Anomalous Scattering Values Found Please Check
7 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 10 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 20 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Program(s) used to solve structure: FOX (Favre-Nicolin & Černý, 2002, 2004).

Phenol-d6 hemideuterate top
Crystal data top
C6D6O·0.5D2OV = 1137.52 (1) Å3
Mr = 110.16Z = 8
Orthorhombic, PbcnF(000) = 440.0
Hall symbol: -P 2n 2abDx = 1.286 Mg m3
a = 13.21570 (2) ÅMelting point: 289 K
b = 10.89240 (2) ÅT = 280 K
c = 7.902113 (15) ÅParticle morphology: fine powder
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2611 (2)0.5384 (3)0.3681 (4)0.06249
D10.2246 (2)0.4652 (4)0.2981 (5)0.09617
C20.3664 (2)0.5482 (4)0.3650 (5)0.07906
D20.4099 (3)0.4827 (5)0.2967 (6)0.12157
C30.4154 (3)0.6429 (3)0.4484 (5)0.07808
D30.4947 (3)0.6522 (4)0.4493 (6)0.11566
C40.3580 (3)0.7277 (4)0.5342 (5)0.07491
D40.3925 (3)0.8022 (5)0.6060 (7)0.13499
C50.2519 (3)0.7205 (4)0.5382 (4)0.06855
D50.2059 (3)0.7837 (4)0.6052 (5)0.10795
C60.2043 (2)0.6255 (3)0.4538 (4)0.06001
O10.1012 (3)0.6199 (4)0.4663 (6)0.07452
D70.0767 (3)0.5638 (5)0.3808 (6)0.08765
Ow10.00.4584 (7)0.250.06156
Dw10.0326 (3)0.4065 (4)0.1647 (6)0.09388
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.075 (3)0.047 (2)0.066 (3)0.0009 (17)0.0008 (18)0.0091 (17)
D10.075 (3)0.092 (3)0.121 (4)0.004 (2)0.0041 (18)0.049 (3)
C20.051 (3)0.081 (3)0.105 (4)0.013 (2)0.013 (2)0.001 (2)
D20.079 (3)0.140 (5)0.145 (4)0.036 (3)0.008 (2)0.046 (3)
C30.052 (2)0.088 (3)0.094 (3)0.010 (2)0.011 (2)0.001 (2)
D30.051 (2)0.135 (4)0.161 (4)0.003 (2)0.005 (3)0.005 (3)
C40.074 (3)0.065 (3)0.086 (3)0.012 (2)0.008 (2)0.023 (2)
D40.111 (3)0.096 (4)0.198 (6)0.025 (3)0.003 (3)0.041 (3)
C50.063 (3)0.077 (3)0.066 (3)0.0008 (18)0.0201 (18)0.009 (2)
D50.076 (2)0.099 (3)0.149 (4)0.005 (2)0.021 (3)0.059 (2)
C60.059 (2)0.059 (2)0.0615 (19)0.0039 (18)0.0016 (18)0.0018 (15)
O10.055 (3)0.085 (4)0.083 (4)0.002 (2)0.009 (2)0.024 (3)
D70.071 (3)0.102 (4)0.090 (3)0.011 (2)0.001 (2)0.012 (2)
Ow10.067 (4)0.076 (5)0.042 (4)0.00.005 (3)0.0
Dw10.078 (2)0.086 (4)0.118 (4)0.009 (2)0.004 (2)0.019 (2)
Geometric parameters (Å, º) top
C1—D11.084 (4)D5—C51.060 (4)
C1—C21.396 (4)D5—C62.098 (5)
C1—C61.387 (4)C6—C11.387 (4)
D1—C11.084 (4)C6—C51.382 (4)
C2—C11.396 (4)C6—D52.098 (5)
C2—D21.063 (4)C6—O11.368 (5)
C2—C31.385 (5)C6—D71.905 (5)
D2—C21.063 (4)O1—C61.368 (5)
C3—C21.385 (5)O1—D70.967 (4)
C3—D31.053 (3)O1—Dw1i1.833 (6)
C3—C41.374 (4)D7—C61.905 (5)
D3—C31.053 (3)D7—O10.967 (4)
D3—C42.096 (5)D7—Ow11.847 (7)
C4—C31.374 (4)Ow1—D71.847 (7)
C4—D32.096 (5)Ow1—D7ii1.847 (7)
C4—D41.091 (4)Ow1—Dw10.980 (4)
C4—C51.405 (4)Ow1—Dw1ii0.980 (4)
D4—C41.091 (4)Dw1—O1iii1.833 (6)
C5—C41.405 (4)Dw1—Ow10.980 (4)
C5—D51.060 (4)Dw1—Dw1ii1.600 (8)
C5—C61.382 (4)
D1—C1—C2119.4 (4)C3—C4—C5121.7 (4)
D1—C1—C6120.8 (4)D4—C4—C5116.6 (4)
C2—C1—C6119.7 (4)C4—C5—D5123.2 (4)
C1—C2—D2119.7 (5)C4—C5—C6119.0 (4)
C1—C2—C3121.0 (4)D5—C5—C6117.8 (4)
D2—C2—C3119.3 (4)C1—C6—C5120.1 (3)
C2—C3—D3122.7 (5)C1—C6—O1123.0 (4)
C2—C3—C4118.5 (4)C5—C6—O1116.9 (4)
D3—C3—C4118.8 (5)C6—O1—D7108.2 (5)
C3—C4—D4121.7 (5)Dw1—Ow1—Dw1ii109.4 (10)
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y, z+1/2; (iii) x, y+1, z1/2.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 ring located at (0.310, 0.634, 0.451).
D—H···AD—HH···AD···AD—H···A
O1—D7···Ow0.97 (1)1.85 (1)2.793 (7)165 (1)
Ow—Dwii···O1iv0.98 (1)1.83 (1)2.746 (5)154 (1)
C1—D1···Cgiii1.08 (1)3.153.844123
C2—D2···Cgiii1.06 (1)3.293.897118
C5—D5···Cgv1.06 (1)2.893.719136
Symmetry codes: (ii) x, y, z+1/2; (iii) x, y+1, z1/2; (iv) x, y+1, z+1; (v) x+1/2, y+3/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds