data_2014699
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o32
_journal_page_last  o34
_publ_section_title
;
Resolution of (S,S)-4-(2,2,4-trimethylchroman-4-yl)phenyl camphanate and its
4-chromanyl epimer by crystallization
;
loop_
_publ_author_name
  'Esterhuysen, Catharine'
  'Bredenkamp, Martin W.'
  'Lloyd, Gareth O.'
_chemical_name_common
;
(S,S)-4-(2,2,4-trimethylchroman-4-yl)phenyl camphanate
;
_chemical_formula_moiety  'C28 H32 O5'
_chemical_formula_sum  'C28 H32 O5'
_chemical_formula_iupac  'C28 H32 O5'
_chemical_formula_weight  448.54
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  7.398(2)
_cell_length_b  8.413(2)
_cell_length_c  38.628(11)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2404.3(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.239
_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 0.7461(2) -0.0724(2) 0.54149(4) 0.0314(4) Uani d . 1 . . O
  O2 0.7800(2) 0.1499(2) 0.73014(4) 0.0245(4) Uani d . 1 . . O
  O3 0.6943(2) 0.4046(2) 0.73977(4) 0.0280(4) Uani d . 1 . . O
  O4 0.8157(2) 0.39592(18) 0.80588(4) 0.0195(4) Uani d . 1 . . O
  O5 0.8294(2) 0.4380(2) 0.86334(4) 0.0255(4) Uani d . 1 . . O
  C1 0.8362(3) 0.0690(3) 0.54357(6) 0.0235(6) Uani d . 1 . . C
  C2 0.9931(4) 0.0783(4) 0.52341(6) 0.0320(7) Uani d . 1 . . C
  H25 1.0324 -0.0105 0.5112 0.038 Uiso calc R 1 . . H
  C3 1.0890(4) 0.2172(4) 0.52148(6) 0.0332(7) Uani d . 1 . . C
  H27 1.1925 0.2223 0.5079 0.040 Uiso calc R 1 . . H
  C4 1.0330(3) 0.3501(3) 0.53965(6) 0.0302(6) Uani d . 1 . . C
  H32 1.0972 0.4449 0.5382 0.036 Uiso calc R 1 . . H
  C5 0.8793(3) 0.3389(3) 0.55998(6) 0.0261(6) Uani d . 1 . . C
  H29 0.8417 0.4282 0.5722 0.031 Uiso calc R 1 . . H
  C6 0.7788(3) 0.2001(3) 0.56290(6) 0.0195(6) Uani d . 1 . . C
  C7 0.6093(3) 0.1908(3) 0.58540(6) 0.0194(5) Uani d . 1 . . C
  C8 0.4951(3) 0.3425(3) 0.58104(6) 0.0253(6) Uani d . 1 . . C
  H26A 0.4793 0.3645 0.5568 0.038 Uiso calc R 1 . . H
  H26B 0.5558 0.4303 0.5919 0.038 Uiso calc R 1 . . H
  H26C 0.3791 0.3274 0.5917 0.038 Uiso calc R 1 . . H
  C9 0.4954(3) 0.0511(3) 0.57215(6) 0.0215(6) Uani d . 1 . . C
  H28A 0.4014 0.0294 0.5890 0.026 Uiso calc R 1 . . H
  H28B 0.4364 0.0836 0.5509 0.026 Uiso calc R 1 . . H
  C10 0.5978(3) -0.1027(3) 0.56523(6) 0.0258(6) Uani d . 1 . . C
  C11 0.6760(4) -0.1793(3) 0.59765(7) 0.0348(7) Uani d . 1 . . C
  H30A 0.7703 -0.1131 0.6068 0.052 Uiso calc R 1 . . H
  H30B 0.7247 -0.2818 0.5919 0.052 Uiso calc R 1 . . H
  H30C 0.5824 -0.1913 0.6147 0.052 Uiso calc R 1 . . H
  C12 0.4780(4) -0.2198(3) 0.54623(7) 0.0382(7) Uani d . 1 . . C
  H33A 0.5459 -0.3141 0.5410 0.057 Uiso calc R 1 . . H
  H33B 0.4357 -0.1726 0.5251 0.057 Uiso calc R 1 . . H
  H33C 0.3766 -0.2470 0.5605 0.057 Uiso calc R 1 . . H
  C13 0.6576(3) 0.1758(3) 0.62422(6) 0.0179(5) Uani d . 1 . . C
  C14 0.8353(3) 0.1798(3) 0.63627(6) 0.0202(5) Uani d . 1 . . C
  H15 0.9299 0.1880 0.6205 0.024 Uiso calc R 1 . . H
  C15 0.8730(3) 0.1719(3) 0.67134(6) 0.0208(5) Uani d . 1 . . C
  H16 0.9921 0.1738 0.6790 0.025 Uiso calc R 1 . . H
  C16 0.7344(3) 0.1612(3) 0.69456(6) 0.0206(5) Uani d . 1 . . C
  C17 0.5573(3) 0.1521(3) 0.68394(6) 0.0246(6) Uani d . 1 . . C
  H22 0.4644 0.1403 0.7000 0.030 Uiso calc R 1 . . H
  C18 0.5202(3) 0.1609(3) 0.64872(6) 0.0234(6) Uani d . 1 . . C
  H12 0.4007 0.1567 0.6413 0.028 Uiso calc R 1 . . H
  C19 0.7613(3) 0.2839(3) 0.74965(6) 0.0203(5) Uani d . 1 . . C
  C20 0.8431(3) 0.2538(3) 0.78465(6) 0.0179(5) Uani d . 1 . . C
  C21 0.8393(3) 0.3476(3) 0.83958(6) 0.0203(5) Uani d . 1 . . C
  C22 0.8803(3) 0.1715(3) 0.83888(6) 0.0204(5) Uani d . 1 . . C
  C23 0.8562(3) 0.0898(3) 0.87344(6) 0.0267(6) Uani d . 1 . . C
  H1A 0.7321 0.0970 0.8805 0.040 Uiso calc R 1 . . H
  H1B 0.9315 0.1404 0.8904 0.040 Uiso calc R 1 . . H
  H1C 0.8899 -0.0200 0.8714 0.040 Uiso calc R 1 . . H
  C24 1.0734(3) 0.1642(3) 0.82325(6) 0.0216(6) Uani d . 1 . . C
  H13A 1.1553 0.2337 0.8357 0.026 Uiso calc R 1 . . H
  H13B 1.1206 0.0566 0.8239 0.026 Uiso calc R 1 . . H
  C25 1.0473(3) 0.2214(3) 0.78539(6) 0.0207(6) Uani d . 1 . . C
  H21A 1.1163 0.3171 0.7807 0.025 Uiso calc R 1 . . H
  H21B 1.0810 0.1397 0.7689 0.025 Uiso calc R 1 . . H
  C26 0.7596(3) 0.1213(3) 0.80769(6) 0.0189(5) Uani d . 1 . . C
  C27 0.5563(3) 0.1452(3) 0.81403(6) 0.0237(6) Uani d . 1 . . C
  H20A 0.5152 0.0706 0.8311 0.036 Uiso calc R 1 . . H
  H20B 0.4915 0.1285 0.7928 0.036 Uiso calc R 1 . . H
  H20C 0.5351 0.2515 0.8221 0.036 Uiso calc R 1 . . H
  C28 0.7910(3) -0.0487(3) 0.79516(6) 0.0230(6) Uani d . 1 . . C
  H17A 0.7655 -0.1216 0.8136 0.035 Uiso calc R 1 . . H
  H17B 0.9145 -0.0606 0.7880 0.035 Uiso calc R 1 . . H
  H17C 0.7126 -0.0706 0.7759 0.035 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 0.0431(11) 0.0225(10) 0.0285(10) 0.0013(9) 0.0088(9) -0.0054(8)
  O2 0.0379(10) 0.0196(9) 0.0159(8) 0.0049(8) -0.0035(8) -0.0026(7)
  O3 0.0398(11) 0.0211(10) 0.0232(9) 0.0058(9) -0.0072(8) -0.0006(8)
  O4 0.0242(9) 0.0175(9) 0.0167(8) 0.0006(8) -0.0013(7) -0.0024(7)
  O5 0.0269(9) 0.0280(10) 0.0217(9) -0.0013(9) -0.0003(8) -0.0101(8)
  C1 0.0311(14) 0.0251(15) 0.0144(12) 0.0045(13) -0.0048(11) 0.0011(11)
  C2 0.0342(16) 0.0424(18) 0.0193(13) 0.0083(15) 0.0020(12) -0.0021(13)
  C3 0.0249(15) 0.055(2) 0.0192(14) 0.0014(14) -0.0008(12) 0.0097(13)
  C4 0.0289(14) 0.0354(17) 0.0263(15) -0.0097(13) -0.0061(12) 0.0096(13)
  C5 0.0275(13) 0.0282(15) 0.0226(13) -0.0020(13) -0.0012(11) 0.0044(12)
  C6 0.0219(12) 0.0235(14) 0.0131(12) 0.0031(11) -0.0035(10) 0.0006(10)
  C7 0.0224(12) 0.0183(13) 0.0174(12) 0.0004(11) -0.0020(10) -0.0001(10)
  C8 0.0288(13) 0.0259(14) 0.0213(13) 0.0039(13) -0.0011(11) -0.0002(11)
  C9 0.0237(13) 0.0254(15) 0.0152(12) -0.0030(12) -0.0027(11) 0.0012(10)
  C10 0.0382(15) 0.0199(14) 0.0192(13) -0.0033(12) -0.0016(12) -0.0019(11)
  C11 0.0539(18) 0.0213(15) 0.0293(14) 0.0020(15) -0.0082(14) 0.0022(12)
  C12 0.0601(19) 0.0258(16) 0.0286(15) -0.0107(15) -0.0091(15) -0.0025(12)
  C13 0.0234(12) 0.0133(12) 0.0169(12) 0.0002(11) 0.0011(10) -0.0017(10)
  C14 0.0232(12) 0.0180(13) 0.0194(12) -0.0002(11) 0.0018(11) -0.0002(11)
  C15 0.0222(13) 0.0184(13) 0.0218(13) 0.0012(12) -0.0043(10) -0.0016(10)
  C16 0.0319(14) 0.0156(12) 0.0142(12) 0.0022(12) -0.0037(11) -0.0018(10)
  C17 0.0296(14) 0.0234(15) 0.0209(13) 0.0032(12) 0.0025(11) -0.0005(11)
  C18 0.0217(13) 0.0241(14) 0.0243(14) 0.0008(12) -0.0023(11) -0.0024(11)
  C19 0.0208(12) 0.0189(13) 0.0213(13) -0.0001(11) 0.0034(11) -0.0014(10)
  C20 0.0222(12) 0.0157(13) 0.0157(12) 0.0017(11) -0.0006(11) -0.0034(10)
  C21 0.0138(11) 0.0288(14) 0.0184(13) -0.0024(12) 0.0007(10) -0.0008(11)
  C22 0.0207(12) 0.0245(14) 0.0159(12) -0.0005(11) -0.0005(10) 0.0018(11)
  C23 0.0301(14) 0.0306(15) 0.0194(13) 0.0008(13) 0.0018(11) 0.0023(11)
  C24 0.0183(12) 0.0266(14) 0.0200(13) 0.0027(12) 0.0000(10) -0.0014(11)
  C25 0.0211(13) 0.0228(14) 0.0181(13) -0.0013(11) 0.0017(10) -0.0002(10)
  C26 0.0188(12) 0.0225(14) 0.0154(12) 0.0022(10) -0.0002(10) 0.0003(10)
  C27 0.0196(12) 0.0247(15) 0.0268(14) -0.0009(11) 0.0009(11) -0.0047(11)
  C28 0.0294(14) 0.0201(13) 0.0196(13) -0.0011(11) 0.0004(11) 0.0000(10)
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 C1 . 1.366(3) ?
  O1 C10 . 1.453(3) ?
  O2 C19 . 1.363(3) ?
  O2 C16 . 1.419(3) ?
  O3 C19 . 1.193(3) ?
  O4 C21 . 1.375(3) ?
  O4 C20 . 1.464(3) ?
  O5 C21 . 1.194(3) ?
  C1 C2 . 1.400(4) ?
  C1 C6 . 1.398(3) ?
  C2 C3 . 1.369(4) ?
  C2 H25 . 0.9300 ?
  C3 C4 . 1.383(4) ?
  C3 H27 . 0.9300 ?
  C4 C5 . 1.385(3) ?
  C4 H32 . 0.9300 ?
  C5 C6 . 1.388(3) ?
  C5 H29 . 0.9300 ?
  C6 C7 . 1.528(3) ?
  C7 C9 . 1.534(3) ?
  C7 C8 . 1.540(3) ?
  C7 C13 . 1.547(3) ?
  C8 H26A . 0.9600 ?
  C8 H26B . 0.9600 ?
  C8 H26C . 0.9600 ?
  C9 C10 . 1.523(4) ?
  C9 H28A . 0.9700 ?
  C9 H28B . 0.9700 ?
  C10 C12 . 1.514(4) ?
  C10 C11 . 1.523(3) ?
  C11 H30A . 0.9600 ?
  C11 H30B . 0.9600 ?
  C11 H30C . 0.9600 ?
  C12 H33A . 0.9600 ?
  C12 H33B . 0.9600 ?
  C12 H33C . 0.9600 ?
  C13 C18 . 1.395(3) ?
  C13 C14 . 1.396(3) ?
  C14 C15 . 1.384(3) ?
  C14 H15 . 0.9300 ?
  C15 C16 . 1.366(3) ?
  C15 H16 . 0.9300 ?
  C16 C17 . 1.375(3) ?
  C17 C18 . 1.390(3) ?
  C17 H22 . 0.9300 ?
  C18 H12 . 0.9300 ?
  C19 C20 . 1.503(3) ?
  C20 C25 . 1.535(3) ?
  C20 C26 . 1.554(3) ?
  C21 C22 . 1.513(4) ?
  C22 C23 . 1.512(3) ?
  C22 C24 . 1.553(3) ?
  C22 C26 . 1.557(3) ?
  C23 H1A . 0.9600 ?
  C23 H1B . 0.9600 ?
  C23 H1C . 0.9600 ?
  C24 C25 . 1.552(3) ?
  C24 H13A . 0.9700 ?
  C24 H13B . 0.9700 ?
  C25 H21A . 0.9700 ?
  C25 H21B . 0.9700 ?
  C26 C28 . 1.528(3) ?
  C26 C27 . 1.538(3) ?
  C27 H20A . 0.9600 ?
  C27 H20B . 0.9600 ?
  C27 H20C . 0.9600 ?
  C28 H17A . 0.9600 ?
  C28 H17B . 0.9600 ?
  C28 H17C . 0.9600 ?