#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2013039.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2013039
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o649
_journal_page_last  o651
_publ_section_title
;
(+-)-6-tert-Butyl-8-hydroxymethyl-2-phenyl-4H-benzo-1,3-dioxine and
2,2,2',2',6,6'-hexamethyl-8,8'-methylenebis(4H-benzo-1,3-dioxine)
;
loop_
_publ_author_name
  'Masci, Bernardo'
  'Levi Mortera, Stefano'
  'Varrone, Maurizio'
  "Thu\'ery, Pierre"
_chemical_formula_moiety  'C19 H22 O3'
_chemical_formula_sum  'C19 H22 O3'
_chemical_formula_weight  298.37
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z+1/2'
  'x+1/2, -y, z'
  '-x+1/2, y, z+1/2'
_cell_length_a  25.6945(15)
_cell_length_b  16.0188(11)
_cell_length_c  7.9750(4)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  3282.5(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.208
_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
  O1A 0.71235(8) 0.20850(14) 0.4164(3) 0.0306(5) Uani d . 1 . . O
  O2A 0.69524(8) 0.34465(13) 0.5049(3) 0.0265(5) Uani d . 1 . . O
  O3A 0.74237(9) 0.56711(13) 0.7321(3) 0.0313(6) Uani d . 1 . . O
  H3A 0.7592 0.6013 0.6548 0.038 Uiso d R 1 . . H
  C1A 0.78433(12) 0.30632(19) 0.4416(4) 0.0257(7) Uani d . 1 . . C
  C2A 0.74820(12) 0.36208(18) 0.5054(4) 0.0240(7) Uani d . 1 . . C
  C3A 0.76308(12) 0.4376(2) 0.5804(4) 0.0246(7) Uani d . 1 . . C
  C4A 0.81579(12) 0.4568(2) 0.5831(4) 0.0256(8) Uani d . 1 . . C
  H4A 0.8264 0.5059 0.6350 0.031 Uiso calc R 1 . . H
  C5A 0.85389(12) 0.4050(2) 0.5105(4) 0.0263(7) Uani d . 1 . . C
  C6A 0.83700(12) 0.3297(2) 0.4431(4) 0.0278(8) Uani d . 1 . . C
  H6A 0.8615 0.2935 0.3973 0.033 Uiso calc R 1 . . H
  C7A 0.76636(12) 0.2235(2) 0.3759(4) 0.0312(8) Uani d . 1 . . C
  H7A1 0.7708 0.2221 0.2551 0.037 Uiso calc R 1 . . H
  H7A2 0.7876 0.1795 0.4238 0.037 Uiso calc R 1 . . H
  C8A 0.72183(13) 0.4957(2) 0.6473(4) 0.0282(8) Uani d . 1 . . C
  H8A1 0.7003 0.5144 0.5548 0.034 Uiso calc R 1 . . H
  H8A2 0.6997 0.4650 0.7242 0.034 Uiso calc R 1 . . H
  C9A 0.91057(12) 0.4348(2) 0.4989(5) 0.0304(8) Uani d . 1 . . C
  C10A 0.94823(13) 0.3626(2) 0.4660(5) 0.0443(10) Uani d . 1 . . C
  H10A 0.9396 0.3363 0.3615 0.066 Uiso calc R 1 . . H
  H10B 0.9456 0.3226 0.5551 0.066 Uiso calc R 1 . . H
  H10C 0.9832 0.3837 0.4607 0.066 Uiso calc R 1 . . H
  C11A 0.91467(14) 0.4978(2) 0.3544(5) 0.0416(9) Uani d . 1 . . C
  H11A 0.9497 0.5184 0.3475 0.062 Uiso calc R 1 . . H
  H11B 0.8913 0.5435 0.3744 0.062 Uiso calc R 1 . . H
  H11C 0.9056 0.4709 0.2509 0.062 Uiso calc R 1 . . H
  C12A 0.92774(14) 0.4790(3) 0.6601(5) 0.0432(10) Uani d . 1 . . C
  H12A 0.9229 0.4423 0.7539 0.065 Uiso calc R 1 . . H
  H12B 0.9072 0.5285 0.6759 0.065 Uiso calc R 1 . . H
  H12C 0.9638 0.4940 0.6515 0.065 Uiso calc R 1 . . H
  C13A 0.68296(12) 0.2814(2) 0.3857(4) 0.0302(8) Uani d . 1 . . C
  H13A 0.6907 0.3020 0.2727 0.036 Uiso calc R 1 . . H
  C14A 0.62598(12) 0.2614(2) 0.3978(4) 0.0289(8) Uani d . 1 . . C
  C15A 0.59165(12) 0.3133(2) 0.4819(4) 0.0350(8) Uani d . 1 . . C
  H15A 0.6044 0.3597 0.5388 0.042 Uiso calc R 1 . . H
  C16A 0.53831(13) 0.2970(2) 0.4827(5) 0.0394(9) Uani d . 1 . . C
  H16A 0.5157 0.3329 0.5385 0.047 Uiso calc R 1 . . H
  C17A 0.51912(14) 0.2277(3) 0.4006(5) 0.0444(10) Uani d . 1 . . C
  H17A 0.4837 0.2162 0.4026 0.053 Uiso calc R 1 . . H
  C18A 0.55274(15) 0.1756(3) 0.3155(5) 0.0448(10) Uani d . 1 . . C
  H18A 0.5398 0.1290 0.2598 0.054 Uiso calc R 1 . . H
  C19A 0.60593(14) 0.1925(2) 0.3125(4) 0.0375(9) Uani d . 1 . . C
  H19A 0.6282 0.1576 0.2533 0.045 Uiso calc R 1 . . H
  O1B 0.72685(9) 1.02626(14) 0.8314(3) 0.0371(6) Uani d . 1 . . O
  O2B 0.69107(9) 0.89325(14) 0.8570(3) 0.0314(5) Uani d . 1 . . O
  O3B 0.70063(8) 0.64609(13) 0.9952(3) 0.0292(5) Uani d . 1 . . O
  H3B 0.7152 0.6228 0.9020 0.035 Uiso d R 1 . . H
  C1B 0.78471(13) 0.9079(2) 0.8313(4) 0.0294(8) Uani d . 1 . . C
  C2B 0.74096(12) 0.86049(19) 0.8658(4) 0.0269(7) Uani d . 1 . . C
  C3B 0.74415(12) 0.77808(19) 0.9187(4) 0.0254(7) Uani d . 1 . . C
  C4B 0.79333(12) 0.7429(2) 0.9371(4) 0.0258(7) Uani d . 1 . . C
  H4B 0.7961 0.6877 0.9718 0.031 Uiso calc R 1 . . H
  C5B 0.83876(12) 0.7882(2) 0.9051(4) 0.0285(8) Uani d . 1 . . C
  C6B 0.83324(13) 0.8705(2) 0.8518(4) 0.0303(8) Uani d . 1 . . C
  H6B 0.8630 0.9016 0.8291 0.036 Uiso calc R 1 . . H
  C7B 0.77770(13) 0.9979(2) 0.7814(5) 0.0368(9) Uani d . 1 . . C
  H7B1 0.8042 1.0319 0.8348 0.044 Uiso calc R 1 . . H
  H7B2 0.7815 1.0034 0.6609 0.044 Uiso calc R 1 . . H
  C8B 0.69430(12) 0.73215(19) 0.9557(4) 0.0296(8) Uani d . 1 . . C
  H8B1 0.6771 0.7594 1.0490 0.036 Uiso calc R 1 . . H
  H8B2 0.6716 0.7368 0.8589 0.036 Uiso calc R 1 . . H
  C9B 0.89296(12) 0.7508(2) 0.9348(4) 0.0324(8) Uani d . 1 . . C
  C10B 0.92441(14) 0.7543(3) 0.7698(4) 0.0413(9) Uani d . 1 . . C
  H10D 0.9587 0.7324 0.7886 0.062 Uiso calc R 1 . . H
  H10E 0.9269 0.8112 0.7325 0.062 Uiso calc R 1 . . H
  H10F 0.9072 0.7216 0.6857 0.062 Uiso calc R 1 . . H
  C11B 0.89039(13) 0.6606(2) 0.9924(5) 0.0444(9) Uani d . 1 . . C
  H11D 0.8734 0.6275 0.9083 0.067 Uiso calc R 1 . . H
  H11E 0.8712 0.6573 1.0954 0.067 Uiso calc R 1 . . H
  H11F 0.9250 0.6398 1.0100 0.067 Uiso calc R 1 . . H
  C12B 0.92143(15) 0.8022(3) 1.0692(5) 0.0445(10) Uani d . 1 . . C
  H12D 0.9023 0.7998 1.1725 0.067 Uiso calc R 1 . . H
  H12E 0.9241 0.8592 1.0329 0.067 Uiso calc R 1 . . H
  H12F 0.9557 0.7797 1.0862 0.067 Uiso calc R 1 . . H
  C13B 0.68815(14) 0.9716(2) 0.7748(4) 0.0336(8) Uani d . 1 . . C
  H13B 0.6920 0.9633 0.6536 0.040 Uiso calc R 1 . . H
  C14B 0.63535(14) 1.0086(2) 0.8106(4) 0.0335(8) Uani d . 1 . . C
  C15B 0.59997(14) 0.9701(2) 0.9149(5) 0.0442(10) Uani d . 1 . . C
  H15B 0.6086 0.9200 0.9671 0.053 Uiso calc R 1 . . H
  C16B 0.55138(15) 1.0060(3) 0.9423(6) 0.0528(11) Uani d . 1 . . C
  H16B 0.5272 0.9795 1.0109 0.063 Uiso calc R 1 . . H
  C17B 0.53926(17) 1.0811(3) 0.8670(6) 0.0557(12) Uani d . 1 . . C
  H17B 0.5070 1.1056 0.8864 0.067 Uiso calc R 1 . . H
  C18B 0.57460(17) 1.1202(3) 0.7632(5) 0.0543(12) Uani d . 1 . . C
  H18B 0.5662 1.1709 0.7129 0.065 Uiso calc R 1 . . H
  C19B 0.62273(15) 1.0838(2) 0.7340(5) 0.0429(10) Uani d . 1 . . C
  H19B 0.6465 1.1097 0.6631 0.051 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
  O1A 0.0298(12) 0.0278(13) 0.0341(13) -0.0021(10) -0.0007(11) -0.0013(10)
  O2A 0.0221(12) 0.0287(12) 0.0287(12) -0.0027(9) -0.0013(10) -0.0024(10)
  O3A 0.0347(14) 0.0247(12) 0.0345(13) -0.0042(11) 0.0073(11) -0.0036(11)
  C1A 0.0326(19) 0.0219(17) 0.0225(17) 0.0001(14) 0.0021(14) 0.0017(13)
  C2A 0.0213(17) 0.0246(17) 0.0261(16) -0.0025(13) -0.0012(14) 0.0026(14)
  C3A 0.0238(19) 0.0297(19) 0.0204(16) 0.0009(14) -0.0025(14) 0.0040(14)
  C4A 0.0270(19) 0.0220(18) 0.0278(18) -0.0003(14) 0.0006(15) 0.0009(14)
  C5A 0.0247(17) 0.0283(19) 0.0260(16) 0.0029(14) -0.0004(14) 0.0034(15)
  C6A 0.0273(18) 0.0301(19) 0.0260(18) 0.0052(15) 0.0021(14) -0.0004(14)
  C7A 0.0306(19) 0.0296(19) 0.0335(19) 0.0025(15) 0.0028(15) -0.0014(15)
  C8A 0.0272(19) 0.0251(19) 0.0324(18) -0.0010(15) 0.0000(14) -0.0028(15)
  C9A 0.0209(17) 0.034(2) 0.0367(18) 0.0012(14) -0.0001(15) 0.0011(17)
  C10A 0.0244(19) 0.044(2) 0.065(3) 0.0052(17) -0.0007(18) -0.004(2)
  C11A 0.033(2) 0.049(2) 0.043(2) -0.0046(18) 0.0001(17) 0.009(2)
  C12A 0.032(2) 0.054(3) 0.043(2) -0.0101(19) -0.0026(18) -0.0021(19)
  C13A 0.0343(19) 0.0254(19) 0.0309(19) -0.0028(15) -0.0039(16) -0.0043(15)
  C14A 0.0277(18) 0.034(2) 0.0254(18) -0.0060(15) -0.0043(15) 0.0025(15)
  C15A 0.0289(19) 0.043(2) 0.0327(19) -0.0062(16) 0.0008(16) -0.0001(17)
  C16A 0.030(2) 0.053(2) 0.035(2) -0.0040(18) 0.0032(17) 0.0026(18)
  C17A 0.029(2) 0.064(3) 0.040(2) -0.014(2) -0.0033(18) 0.006(2)
  C18A 0.038(2) 0.056(3) 0.041(2) -0.017(2) -0.0104(19) 0.0006(19)
  C19A 0.036(2) 0.041(2) 0.036(2) -0.0064(17) -0.0001(17) -0.0013(17)
  O1B 0.0414(15) 0.0253(13) 0.0444(15) -0.0014(11) 0.0023(12) 0.0009(11)
  O2B 0.0279(12) 0.0245(13) 0.0416(14) 0.0060(10) -0.0021(11) 0.0010(11)
  O3B 0.0289(12) 0.0251(12) 0.0335(12) 0.0013(10) 0.0037(11) 0.0017(10)
  C1B 0.0317(19) 0.0285(19) 0.0279(18) 0.0012(15) 0.0021(15) 0.0012(15)
  C2B 0.0239(17) 0.0268(18) 0.0300(18) 0.0039(15) 0.0021(15) -0.0017(14)
  C3B 0.0224(17) 0.0264(18) 0.0273(17) -0.0007(14) -0.0027(15) -0.0011(14)
  C4B 0.0250(17) 0.0254(17) 0.0271(17) -0.0003(14) 0.0006(14) 0.0001(14)
  C5B 0.0245(17) 0.034(2) 0.0268(17) -0.0019(15) -0.0009(15) -0.0029(15)
  C6B 0.0275(18) 0.034(2) 0.0291(17) -0.0069(15) 0.0050(15) -0.0031(15)
  C7B 0.038(2) 0.031(2) 0.042(2) -0.0022(17) 0.0076(17) -0.0010(16)
  C8B 0.0276(19) 0.0241(18) 0.037(2) 0.0006(14) 0.0009(15) -0.0005(14)
  C9B 0.0200(17) 0.044(2) 0.0333(19) -0.0018(15) -0.0010(15) 0.0008(17)
  C10B 0.0240(19) 0.060(3) 0.040(2) 0.0072(18) 0.0044(17) -0.0017(19)
  C11B 0.0261(19) 0.047(2) 0.060(2) 0.0087(17) 0.0008(19) 0.009(2)
  C12B 0.032(2) 0.065(3) 0.037(2) -0.0026(19) -0.0041(17) -0.0034(19)
  C13B 0.040(2) 0.026(2) 0.034(2) 0.0047(16) -0.0035(17) 0.0020(16)
  C14B 0.039(2) 0.029(2) 0.033(2) 0.0079(17) -0.0034(16) -0.0029(15)
  C15B 0.042(2) 0.044(2) 0.046(2) 0.0134(18) 0.001(2) 0.0022(19)
  C16B 0.043(2) 0.058(3) 0.057(3) 0.013(2) 0.007(2) -0.004(2)
  C17B 0.050(3) 0.052(3) 0.066(3) 0.026(2) -0.004(2) -0.006(2)
  C18B 0.056(3) 0.051(3) 0.056(3) 0.022(2) -0.011(2) 0.003(2)
  C19B 0.052(3) 0.035(2) 0.042(2) 0.0046(19) -0.0083(19) 0.0025(17)
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
  O1A C13A . 1.412(4) ?
  O1A C7A . 1.445(4) ?
  O2A C2A . 1.389(3) ?
  O2A C13A . 1.424(4) ?
  O3A C8A . 1.430(4) ?
  O3A H3A . 0.9304 ?
  C1A C2A . 1.385(4) ?
  C1A C6A . 1.404(4) ?
  C1A C7A . 1.499(4) ?
  C2A C3A . 1.403(4) ?
  C3A C4A . 1.389(4) ?
  C3A C8A . 1.508(4) ?
  C4A C5A . 1.408(4) ?
  C4A H4A . 0.9300 ?
  C5A C6A . 1.390(4) ?
  C5A C9A . 1.535(4) ?
  C6A H6A . 0.9300 ?
  C7A H7A1 . 0.9700 ?
  C7A H7A2 . 0.9700 ?
  C8A H8A1 . 0.9700 ?
  C8A H8A2 . 0.9700 ?
  C9A C10A . 1.530(5) ?
  C9A C12A . 1.533(5) ?
  C9A C11A . 1.536(5) ?
  C10A H10A . 0.9600 ?
  C10A H10B . 0.9600 ?
  C10A H10C . 0.9600 ?
  C11A H11A . 0.9600 ?
  C11A H11B . 0.9600 ?
  C11A H11C . 0.9600 ?
  C12A H12A . 0.9600 ?
  C12A H12B . 0.9600 ?
  C12A H12C . 0.9600 ?
  C13A C14A . 1.502(4) ?
  C13A H13A . 0.9800 ?
  C14A C15A . 1.385(5) ?
  C14A C19A . 1.395(5) ?
  C15A C16A . 1.395(4) ?
  C15A H15A . 0.9300 ?
  C16A C17A . 1.380(5) ?
  C16A H16A . 0.9300 ?
  C17A C18A . 1.379(5) ?
  C17A H17A . 0.9300 ?
  C18A C19A . 1.393(5) ?
  C18A H18A . 0.9300 ?
  C19A H19A . 0.9300 ?
  O1B C13B . 1.400(4) ?
  O1B C7B . 1.440(4) ?
  O2B C2B . 1.387(4) ?
  O2B C13B . 1.418(4) ?
  O3B C8B . 1.424(4) ?
  O3B H3B . 0.9123 ?
  C1B C2B . 1.384(4) ?
  C1B C6B . 1.393(5) ?
  C1B C7B . 1.506(5) ?
  C2B C3B . 1.388(4) ?
  C3B C4B . 1.391(4) ?
  C3B C8B . 1.506(4) ?
  C4B C5B . 1.397(4) ?
  C4B H4B . 0.9300 ?
  C5B C6B . 1.393(4) ?
  C5B C9B . 1.534(4) ?
  C6B H6B . 0.9300 ?
  C7B H7B1 . 0.9700 ?
  C7B H7B2 . 0.9700 ?
  C8B H8B1 . 0.9700 ?
  C8B H8B2 . 0.9700 ?
  C9B C11B . 1.518(5) ?
  C9B C12B . 1.537(5) ?
  C9B C10B . 1.545(5) ?
  C10B H10D . 0.9600 ?
  C10B H10E . 0.9600 ?
  C10B H10F . 0.9600 ?
  C11B H11D . 0.9600 ?
  C11B H11E . 0.9600 ?
  C11B H11F . 0.9600 ?
  C12B H12D . 0.9600 ?
  C12B H12E . 0.9600 ?
  C12B H12F . 0.9600 ?
  C13B C14B . 1.508(5) ?
  C13B H13B . 0.9800 ?
  C14B C15B . 1.378(5) ?
  C14B C19B . 1.389(5) ?
  C15B C16B . 1.392(5) ?
  C15B H15B . 0.9300 ?
  C16B C17B . 1.381(6) ?
  C16B H16B . 0.9300 ?
  C17B C18B . 1.379(6) ?
  C17B H17B . 0.9300 ?
  C18B C19B . 1.387(5) ?
  C18B H18B . 0.9300 ?
  C19B H19B . 0.9300 ?
_cod_database_code 2013039