data_2012934
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o575
_journal_page_last  o579
_publ_section_title
;
Hydrogen-bonded assemblages in 2,6-bis(hydroxymethyl)-4-R-phenol with R =
methyl, methoxy, phenoxy and 1-(4-methoxyphenyl)-1-methylethyl
;
loop_
_publ_author_name
  'Masci, Bernardo'
  'Thu\'ery, Pierre'
_chemical_formula_moiety  'C14 H14 O4'
_chemical_formula_sum  'C14 H14 O4'
_chemical_formula_iupac  'C14 H14 O4'
_chemical_formula_weight  246.25
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  11.1451(11)
_cell_length_b  13.5515(12)
_cell_length_c  8.1935(9)
_cell_angle_alpha  90.00
_cell_angle_beta  97.486(6)
_cell_angle_gamma  90.00
_cell_volume  1226.9(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.333
_diffrn_ambient_temperature  100(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  O1 -0.0185(2) 0.91081(18) 0.0823(3) 0.0296(6) Uani d . 1 . . O
  H1 -0.0518 0.8833 0.1586 0.035 Uiso d R 1 . . H
  O2 0.0828(2) 1.10527(16) 0.2397(3) 0.0286(6) Uani d . 1 . . O
  H2 0.0605 1.0834 0.1347 0.034 Uiso d R 1 . . H
  O3 0.1490(2) 1.19638(17) 0.7209(3) 0.0290(6) Uani d . 1 . . O
  H3 0.1081 1.2576 0.7364 0.035 Uiso d R 1 . . H
  O4 0.2683(2) 0.84138(17) 0.7230(3) 0.0298(6) Uani d . 1 . . O
  C1 0.1386(3) 0.9358(3) 0.3159(4) 0.0257(8) Uani d . 1 . . C
  C2 0.1236(3) 1.0346(2) 0.3543(4) 0.0233(8) Uani d . 1 . . C
  C3 0.1542(3) 1.0699(3) 0.5157(4) 0.0249(8) Uani d . 1 . . C
  C4 0.2024(3) 1.0048(3) 0.6364(4) 0.0257(8) Uani d . 1 . . C
  H4 0.2240 1.0270 0.7436 0.031 Uiso calc R 1 . . H
  C5 0.2188(3) 0.9064(3) 0.5987(4) 0.0266(8) Uani d . 1 . . C
  C6 0.1865(3) 0.8715(3) 0.4418(4) 0.0268(8) Uani d . 1 . . C
  H6 0.1964 0.8050 0.4190 0.032 Uiso calc R 1 . . H
  C7 0.1076(3) 0.8986(3) 0.1424(4) 0.0292(9) Uani d . 1 . . C
  H7A 0.1556 0.9339 0.0709 0.035 Uiso calc R 1 . . H
  H7B 0.1284 0.8292 0.1387 0.035 Uiso calc R 1 . . H
  C8 0.1385(3) 1.1774(3) 0.5484(4) 0.0286(9) Uani d . 1 . . C
  H8A 0.1995 1.2148 0.5007 0.034 Uiso calc R 1 . . H
  H8B 0.0596 1.1988 0.4965 0.034 Uiso calc R 1 . . H
  C9 0.3891(3) 0.8594(3) 0.7865(4) 0.0266(9) Uani d . 1 . . C
  C10 0.4704(3) 0.9005(3) 0.6931(5) 0.0339(9) Uani d . 1 . . C
  H10 0.4459 0.9185 0.5844 0.041 Uiso calc R 1 . . H
  C11 0.5888(4) 0.9146(3) 0.7625(5) 0.0417(11) Uani d . 1 . . C
  H11 0.6434 0.9439 0.7008 0.050 Uiso calc R 1 . . H
  C12 0.6273(4) 0.8857(3) 0.9235(5) 0.0401(11) Uani d . 1 . . C
  H12 0.7076 0.8941 0.9685 0.048 Uiso calc R 1 . . H
  C13 0.5459(4) 0.8446(3) 1.0152(5) 0.0426(11) Uani d . 1 . . C
  H13 0.5712 0.8253 1.1231 0.051 Uiso calc R 1 . . H
  C14 0.4249(3) 0.8313(3) 0.9479(5) 0.0359(10) Uani d . 1 . . C
  H14 0.3695 0.8040 1.0106 0.043 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1 0.0282(15) 0.0342(14) 0.0251(13) -0.0040(11) -0.0012(11) 0.0045(11)
  O2 0.0371(16) 0.0270(14) 0.0194(12) -0.0013(11) -0.0045(11) 0.0028(11)
  O3 0.0412(16) 0.0254(13) 0.0200(13) 0.0020(11) 0.0025(11) -0.0026(11)
  O4 0.0242(14) 0.0293(14) 0.0330(14) 0.0001(11) -0.0069(11) 0.0077(11)
  C1 0.023(2) 0.031(2) 0.0234(18) -0.0039(15) 0.0016(15) -0.0021(16)
  C2 0.021(2) 0.0243(18) 0.0236(19) 0.0023(14) 0.0004(15) 0.0038(16)
  C3 0.025(2) 0.0260(19) 0.0240(19) -0.0033(15) 0.0032(15) -0.0024(15)
  C4 0.027(2) 0.0273(19) 0.0218(19) -0.0029(15) -0.0001(15) -0.0020(16)
  C5 0.0221(19) 0.0279(19) 0.0276(19) 0.0034(15) -0.0052(15) 0.0040(17)
  C6 0.024(2) 0.0250(19) 0.030(2) -0.0012(15) -0.0009(16) -0.0022(16)
  C7 0.030(2) 0.029(2) 0.028(2) 0.0019(16) 0.0029(17) -0.0025(17)
  C8 0.037(2) 0.029(2) 0.0189(18) -0.0011(16) 0.0003(16) 0.0008(16)
  C9 0.021(2) 0.0264(19) 0.031(2) 0.0021(15) -0.0019(16) 0.0002(16)
  C10 0.026(2) 0.038(2) 0.035(2) -0.0012(17) -0.0009(17) 0.0007(18)
  C11 0.028(2) 0.051(3) 0.047(3) -0.0023(19) 0.007(2) 0.003(2)
  C12 0.026(2) 0.041(2) 0.050(3) 0.0033(18) -0.0068(19) -0.007(2)
  C13 0.041(3) 0.043(2) 0.040(2) -0.002(2) -0.010(2) 0.004(2)
  C14 0.031(2) 0.037(2) 0.037(2) -0.0056(17) -0.0068(18) 0.0064(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C7 . 1.437(4) ?
  O1 H1 . 0.8528 ?
  O2 C2 . 1.375(4) ?
  O2 H2 . 0.9139 ?
  O3 C8 . 1.427(4) ?
  O3 H3 . 0.9632 ?
  O4 C9 . 1.400(4) ?
  O4 C5 . 1.404(4) ?
  C1 C2 . 1.391(5) ?
  C1 C6 . 1.402(5) ?
  C1 C7 . 1.506(5) ?
  C2 C3 . 1.405(5) ?
  C3 C4 . 1.381(5) ?
  C3 C8 . 1.496(5) ?
  C4 C5 . 1.385(5) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.373(5) ?
  C6 H6 . 0.9300 ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 H8A . 0.9700 ?
  C8 H8B . 0.9700 ?
  C9 C10 . 1.378(5) ?
  C9 C14 . 1.384(5) ?
  C10 C11 . 1.380(5) ?
  C10 H10 . 0.9300 ?
  C11 C12 . 1.389(5) ?
  C11 H11 . 0.9300 ?
  C12 C13 . 1.370(6) ?
  C12 H12 . 0.9300 ?
  C13 C14 . 1.401(5) ?
  C13 H13 . 0.9300 ?
  C14 H14 . 0.9300 ?