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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.
Keywords: phenol; hydrate; neutron powder diffraction; thermal expansion; DFT; Hirshfeld surface analysis.
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020007719/wm5564sup1.cif |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2056989020007719/wm5564sup2.pdf |
![]() | Text file https://doi.org/10.1107/S2056989020007719/wm5564sup3.txt |
CCDC reference: 2008230
Key indicators
- Single-crystal X-ray study
- T = 280 K
- Mean
(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
Phenol-d6 hemideuterate top
Crystal data top
C6D6O·0.5D2O | V = 1137.52 (1) Å3 |
Mr = 110.16 | Z = 8 |
Orthorhombic, Pbcn | F(000) = 440.0 |
Hall symbol: -P 2n 2ab | Dx = 1.286 Mg m−3 |
a = 13.21570 (2) Å | Melting point: 289 K |
b = 10.89240 (2) Å | T = 280 K |
c = 7.902113 (15) Å | Particle morphology: fine powder |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.2611 (2) | 0.5384 (3) | 0.3681 (4) | 0.06249 | |
D1 | 0.2246 (2) | 0.4652 (4) | 0.2981 (5) | 0.09617 | |
C2 | 0.3664 (2) | 0.5482 (4) | 0.3650 (5) | 0.07906 | |
D2 | 0.4099 (3) | 0.4827 (5) | 0.2967 (6) | 0.12157 | |
C3 | 0.4154 (3) | 0.6429 (3) | 0.4484 (5) | 0.07808 | |
D3 | 0.4947 (3) | 0.6522 (4) | 0.4493 (6) | 0.11566 | |
C4 | 0.3580 (3) | 0.7277 (4) | 0.5342 (5) | 0.07491 | |
D4 | 0.3925 (3) | 0.8022 (5) | 0.6060 (7) | 0.13499 | |
C5 | 0.2519 (3) | 0.7205 (4) | 0.5382 (4) | 0.06855 | |
D5 | 0.2059 (3) | 0.7837 (4) | 0.6052 (5) | 0.10795 | |
C6 | 0.2043 (2) | 0.6255 (3) | 0.4538 (4) | 0.06001 | |
O1 | 0.1012 (3) | 0.6199 (4) | 0.4663 (6) | 0.07452 | |
D7 | 0.0767 (3) | 0.5638 (5) | 0.3808 (6) | 0.08765 | |
Ow1 | 0.0 | 0.4584 (7) | 0.25 | 0.06156 | |
Dw1 | 0.0326 (3) | 0.4065 (4) | 0.1647 (6) | 0.09388 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.075 (3) | 0.047 (2) | 0.066 (3) | −0.0009 (17) | −0.0008 (18) | −0.0091 (17) |
D1 | 0.075 (3) | 0.092 (3) | 0.121 (4) | −0.004 (2) | 0.0041 (18) | −0.049 (3) |
C2 | 0.051 (3) | 0.081 (3) | 0.105 (4) | 0.013 (2) | 0.013 (2) | 0.001 (2) |
D2 | 0.079 (3) | 0.140 (5) | 0.145 (4) | 0.036 (3) | 0.008 (2) | −0.046 (3) |
C3 | 0.052 (2) | 0.088 (3) | 0.094 (3) | −0.010 (2) | −0.011 (2) | 0.001 (2) |
D3 | 0.051 (2) | 0.135 (4) | 0.161 (4) | −0.003 (2) | −0.005 (3) | −0.005 (3) |
C4 | 0.074 (3) | 0.065 (3) | 0.086 (3) | −0.012 (2) | 0.008 (2) | −0.023 (2) |
D4 | 0.111 (3) | 0.096 (4) | 0.198 (6) | −0.025 (3) | 0.003 (3) | −0.041 (3) |
C5 | 0.063 (3) | 0.077 (3) | 0.066 (3) | 0.0008 (18) | 0.0201 (18) | −0.009 (2) |
D5 | 0.076 (2) | 0.099 (3) | 0.149 (4) | −0.005 (2) | 0.021 (3) | −0.059 (2) |
C6 | 0.059 (2) | 0.059 (2) | 0.0615 (19) | −0.0039 (18) | 0.0016 (18) | 0.0018 (15) |
O1 | 0.055 (3) | 0.085 (4) | 0.083 (4) | 0.002 (2) | 0.009 (2) | −0.024 (3) |
D7 | 0.071 (3) | 0.102 (4) | 0.090 (3) | 0.011 (2) | −0.001 (2) | −0.012 (2) |
Ow1 | 0.067 (4) | 0.076 (5) | 0.042 (4) | 0.0 | 0.005 (3) | 0.0 |
Dw1 | 0.078 (2) | 0.086 (4) | 0.118 (4) | 0.009 (2) | 0.004 (2) | −0.019 (2) |
Geometric parameters (Å, º) top
C1—D1 | 1.084 (4) | D5—C5 | 1.060 (4) |
C1—C2 | 1.396 (4) | D5—C6 | 2.098 (5) |
C1—C6 | 1.387 (4) | C6—C1 | 1.387 (4) |
D1—C1 | 1.084 (4) | C6—C5 | 1.382 (4) |
C2—C1 | 1.396 (4) | C6—D5 | 2.098 (5) |
C2—D2 | 1.063 (4) | C6—O1 | 1.368 (5) |
C2—C3 | 1.385 (5) | C6—D7 | 1.905 (5) |
D2—C2 | 1.063 (4) | O1—C6 | 1.368 (5) |
C3—C2 | 1.385 (5) | O1—D7 | 0.967 (4) |
C3—D3 | 1.053 (3) | O1—Dw1i | 1.833 (6) |
C3—C4 | 1.374 (4) | D7—C6 | 1.905 (5) |
D3—C3 | 1.053 (3) | D7—O1 | 0.967 (4) |
D3—C4 | 2.096 (5) | D7—Ow1 | 1.847 (7) |
C4—C3 | 1.374 (4) | Ow1—D7 | 1.847 (7) |
C4—D3 | 2.096 (5) | Ow1—D7ii | 1.847 (7) |
C4—D4 | 1.091 (4) | Ow1—Dw1 | 0.980 (4) |
C4—C5 | 1.405 (4) | Ow1—Dw1ii | 0.980 (4) |
D4—C4 | 1.091 (4) | Dw1—O1iii | 1.833 (6) |
C5—C4 | 1.405 (4) | Dw1—Ow1 | 0.980 (4) |
C5—D5 | 1.060 (4) | Dw1—Dw1ii | 1.600 (8) |
C5—C6 | 1.382 (4) | ||
D1—C1—C2 | 119.4 (4) | C3—C4—C5 | 121.7 (4) |
D1—C1—C6 | 120.8 (4) | D4—C4—C5 | 116.6 (4) |
C2—C1—C6 | 119.7 (4) | C4—C5—D5 | 123.2 (4) |
C1—C2—D2 | 119.7 (5) | C4—C5—C6 | 119.0 (4) |
C1—C2—C3 | 121.0 (4) | D5—C5—C6 | 117.8 (4) |
D2—C2—C3 | 119.3 (4) | C1—C6—C5 | 120.1 (3) |
C2—C3—D3 | 122.7 (5) | C1—C6—O1 | 123.0 (4) |
C2—C3—C4 | 118.5 (4) | C5—C6—O1 | 116.9 (4) |
D3—C3—C4 | 118.8 (5) | C6—O1—D7 | 108.2 (5) |
C3—C4—D4 | 121.7 (5) | Dw1—Ow1—Dw1ii | 109.4 (10) |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x, y, −z+1/2; (iii) x, −y+1, z−1/2. |
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···A | D—H | H···A | D···A | D—H···A |
O1—D7···Ow | 0.97 (1) | 1.85 (1) | 2.793 (7) | 165 (1) |
Ow—Dwii···O1iv | 0.98 (1) | 1.83 (1) | 2.746 (5) | 154 (1) |
C1—D1···Cgiii | 1.08 (1) | 3.15 | 3.844 | 123 |
C2—D2···Cgiii | 1.06 (1) | 3.29 | 3.897 | 118 |
C5—D5···Cgv | 1.06 (1) | 2.89 | 3.719 | 136 |
Symmetry codes: (ii) −x, y, −z+1/2; (iii) x, −y+1, z−1/2; (iv) −x, −y+1, −z+1; (v) −x+1/2, −y+3/2, z+1/2. |