# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Mike Zaworotko' 'Jennifer A. McMahon' 'Julius F. Remenar' _publ_contact_author_name 'Prof Mike Zaworotko' _publ_contact_author_address ; Department of Chemistry University of South Florida SCA400 4202 E. Fowler Avenue Tampa Florida 33620 UNITED STATES OF AMERICA ; _publ_contact_author_email XTAL@USF.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Polymorphism in butylated hydroxy anisole (BHA) ; data_tp0510s _database_code_CSD 220677 _audit_creation_method SHELXL-97 _chemical_name_systematic 3-tert-Butyl-4-hydroxyanisole _chemical_name_common BHA _chemical_melting_point '61 C' _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 O2' _chemical_formula_weight 180.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3179(11) _cell_length_b 14.364(3) _cell_length_c 17.960(3) _cell_angle_alpha 74.636(3) _cell_angle_beta 80.608(4) _cell_angle_gamma 86.767(3) _cell_volume 1550.5(5) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour ? _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9729 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 28.24 _reflns_number_total 6805 _reflns_number_gt 4642 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6805 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1618 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.1844(2) 0.93323(10) 0.62633(8) 0.0294(4) Uani 1 1 d . . . O2 O 0.4016(2) 0.69011(10) 0.50540(8) 0.0260(3) Uani 1 1 d . . . H1 H 0.4716 0.6564 0.5368 0.031 Uiso 1 1 d R . . C1 C -0.0457(3) 0.87071(14) 0.59445(12) 0.0236(4) Uani 1 1 d . . . C2 C 0.1177(3) 0.82936(15) 0.63609(12) 0.0254(5) Uani 1 1 d . . . H2 H 0.1285 0.8426 0.6844 0.030 Uiso 1 1 calc R . . C3 C 0.2645(3) 0.76858(14) 0.60603(11) 0.0236(4) Uani 1 1 d . . . H3 H 0.3775 0.7403 0.6340 0.028 Uiso 1 1 calc R . . C4 C 0.2497(3) 0.74804(13) 0.53568(11) 0.0207(4) Uani 1 1 d . . . C5 C 0.0823(3) 0.78703(13) 0.49360(11) 0.0208(4) Uani 1 1 d . . . C6 C -0.0626(3) 0.84914(14) 0.52492(11) 0.0224(4) Uani 1 1 d . . . H6 H -0.1766 0.8775 0.4976 0.027 Uiso 1 1 calc R . . C7 C -0.3559(4) 0.97644(16) 0.58491(13) 0.0315(5) Uani 1 1 d . . . H71 H -0.4387 1.0143 0.6153 0.038 Uiso 1 1 d R . . H72 H -0.4452 0.9262 0.5803 0.038 Uiso 1 1 d R . . H73 H -0.3063 1.0173 0.5300 0.038 Uiso 1 1 d R . . C8 C 0.0555(3) 0.76181(14) 0.41739(11) 0.0224(4) Uani 1 1 d . . . C9 C 0.2499(4) 0.79639(16) 0.35397(12) 0.0279(5) Uani 1 1 d . . . H74 H 0.2584 0.8758 0.3341 0.033 Uiso 1 1 d R . . H75 H 0.2364 0.7722 0.3081 0.033 Uiso 1 1 d R . . H76 H 0.3725 0.7734 0.3678 0.033 Uiso 1 1 d R . . C10 C 0.0290(4) 0.65266(14) 0.43354(12) 0.0287(5) Uani 1 1 d . . . H77 H 0.0232 0.6283 0.3910 0.034 Uiso 1 1 d R . . H78 H 0.1551 0.6141 0.4486 0.034 Uiso 1 1 d R . . H79 H -0.1006 0.6319 0.4702 0.034 Uiso 1 1 d R . . C11 C -0.1442(4) 0.81060(16) 0.38534(12) 0.0307(5) Uani 1 1 d . . . H80 H -0.2739 0.7865 0.4267 0.037 Uiso 1 1 d R . . H81 H -0.1348 0.8800 0.3737 0.037 Uiso 1 1 d R . . H82 H -0.1666 0.7926 0.3383 0.037 Uiso 1 1 d R . . O101 O 0.4628(2) 0.46388(10) 0.38875(8) 0.0274(3) Uani 1 1 d . . . O102 O -0.0128(2) 0.55815(9) 0.14607(8) 0.0240(3) Uani 1 1 d . . . H101 H -0.0698 0.5056 0.1409 0.029 Uiso 1 1 d R . . C101 C 0.3540(3) 0.48824(13) 0.32504(11) 0.0212(4) Uani 1 1 d . . . C102 C 0.1897(3) 0.42780(13) 0.32599(12) 0.0226(4) Uani 1 1 d . . . H102 H 0.1594 0.3713 0.3676 0.027 Uiso 1 1 calc R . . C103 C 0.0705(3) 0.45129(13) 0.26517(11) 0.0220(4) Uani 1 1 d . . . H103 H -0.0432 0.4106 0.2654 0.026 Uiso 1 1 calc R . . C104 C 0.1150(3) 0.53371(13) 0.20367(11) 0.0191(4) Uani 1 1 d . . . C105 C 0.2861(3) 0.59345(13) 0.20047(11) 0.0186(4) Uani 1 1 d . . . C106 C 0.4017(3) 0.56875(13) 0.26292(12) 0.0212(4) Uani 1 1 d . . . H106 H 0.5170 0.6085 0.2629 0.025 Uiso 1 1 calc R . . C107 C 0.6180(4) 0.53059(15) 0.39237(13) 0.0279(5) Uani 1 1 d . . . H107 H 0.6733 0.5047 0.4385 0.033 Uiso 1 1 d R . . H108 H 0.7350 0.5403 0.3505 0.033 Uiso 1 1 d R . . H109 H 0.5635 0.5944 0.3939 0.033 Uiso 1 1 d R . . C108 C 0.3490(3) 0.68085(13) 0.13066(12) 0.0221(4) Uani 1 1 d . . . C109 C 0.4076(4) 0.64642(16) 0.05601(12) 0.0313(5) Uani 1 1 d . . . H110 H 0.2962 0.6187 0.0439 0.038 Uiso 1 1 d R . . H111 H 0.5252 0.6025 0.0646 0.038 Uiso 1 1 d R . . H112 H 0.4537 0.7008 0.0117 0.038 Uiso 1 1 d R . . C110 C 0.1627(4) 0.75522(14) 0.12250(13) 0.0298(5) Uani 1 1 d . . . H113 H 0.1210 0.7785 0.1734 0.036 Uiso 1 1 d R . . H114 H 0.2128 0.8065 0.0793 0.036 Uiso 1 1 d R . . H115 H 0.0435 0.7255 0.1123 0.036 Uiso 1 1 d R . . C111 C 0.5457(4) 0.73227(15) 0.14030(13) 0.0294(5) Uani 1 1 d . . . H116 H 0.5144 0.7618 0.1894 0.035 Uiso 1 1 d R . . H117 H 0.6698 0.6883 0.1467 0.035 Uiso 1 1 d R . . H118 H 0.5753 0.7819 0.0961 0.035 Uiso 1 1 d R . . O201 O 0.8953(2) 0.39725(9) 0.10647(8) 0.0270(3) Uani 1 1 d . . . O202 O 0.3690(2) 0.07938(10) 0.22236(8) 0.0278(3) Uani 1 1 d . . . H201 H 0.2721 0.0835 0.2654 0.033 Uiso 1 1 d R . . C201 C 0.7724(3) 0.31482(13) 0.13676(11) 0.0207(4) Uani 1 1 d . . . C202 C 0.5775(3) 0.32438(14) 0.18305(12) 0.0235(4) Uani 1 1 d . . . H202 H 0.5353 0.3842 0.1946 0.028 Uiso 1 1 calc R . . C203 C 0.4462(3) 0.24476(14) 0.21191(12) 0.0241(4) Uani 1 1 d . . . H203 H 0.3127 0.2503 0.2437 0.029 Uiso 1 1 calc R . . C204 C 0.5056(3) 0.15678(14) 0.19543(11) 0.0217(4) Uani 1 1 d . . . C205 C 0.7040(3) 0.14545(13) 0.15008(11) 0.0192(4) Uani 1 1 d . . . C206 C 0.8343(3) 0.22663(14) 0.12155(11) 0.0208(4) Uani 1 1 d . . . H206 H 0.9695 0.2212 0.0908 0.025 Uiso 1 1 calc R . . C207 C 1.0961(3) 0.38862(15) 0.05794(13) 0.0284(5) Uani 1 1 d . . . H207 H 1.0707 0.3627 0.0176 0.034 Uiso 1 1 d R . . H208 H 1.1751 0.4479 0.0502 0.034 Uiso 1 1 d R . . H209 H 1.1861 0.3451 0.0886 0.034 Uiso 1 1 d R . . C208 C 0.7781(3) 0.04898(14) 0.13182(11) 0.0223(4) Uani 1 1 d . . . C209 C 1.0021(3) 0.05626(15) 0.08322(12) 0.0258(5) Uani 1 1 d . . . H210 H 1.0163 0.1035 0.0324 0.031 Uiso 1 1 d R . . H211 H 1.1100 0.0703 0.1094 0.031 Uiso 1 1 d R . . H212 H 1.0410 -0.0072 0.0753 0.031 Uiso 1 1 d R . . C210 C 0.7920(4) -0.02862(15) 0.20867(13) 0.0326(5) Uani 1 1 d . . . H213 H 0.6599 -0.0315 0.2421 0.039 Uiso 1 1 d R . . H214 H 0.9005 -0.0135 0.2398 0.039 Uiso 1 1 d R . . H215 H 0.8402 -0.0877 0.1989 0.039 Uiso 1 1 d R . . C211 C 0.6202(4) 0.01812(15) 0.08649(12) 0.0277(5) Uani 1 1 d . . . H216 H 0.6144 0.0689 0.0435 0.033 Uiso 1 1 d R . . H217 H 0.4853 0.0011 0.1200 0.033 Uiso 1 1 d R . . H218 H 0.6795 -0.0414 0.0724 0.033 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0239(8) 0.0369(8) 0.0282(8) -0.0124(7) -0.0007(7) 0.0021(7) O2 0.0239(8) 0.0293(7) 0.0254(7) -0.0060(6) -0.0096(6) 0.0065(6) C1 0.0201(11) 0.0256(10) 0.0234(10) -0.0063(8) 0.0033(8) -0.0043(8) C2 0.0246(12) 0.0336(11) 0.0189(10) -0.0074(9) -0.0030(9) -0.0062(9) C3 0.0212(11) 0.0269(10) 0.0225(10) -0.0031(8) -0.0082(9) -0.0020(8) C4 0.0182(11) 0.0214(9) 0.0214(10) -0.0032(8) -0.0035(8) -0.0026(8) C5 0.0185(11) 0.0245(10) 0.0182(9) -0.0023(8) -0.0034(8) -0.0037(8) C6 0.0164(11) 0.0271(10) 0.0216(10) -0.0024(8) -0.0027(8) -0.0030(8) C7 0.0226(12) 0.0332(11) 0.0399(13) -0.0130(10) -0.0033(10) 0.0022(9) C8 0.0192(11) 0.0285(10) 0.0194(10) -0.0046(8) -0.0044(8) -0.0020(8) C9 0.0226(12) 0.0401(12) 0.0220(10) -0.0086(9) -0.0044(9) -0.0033(9) C10 0.0275(13) 0.0318(11) 0.0294(11) -0.0111(9) -0.0055(10) -0.0032(9) C11 0.0271(13) 0.0434(12) 0.0229(11) -0.0064(10) -0.0116(9) 0.0004(10) O101 0.0271(9) 0.0281(7) 0.0284(8) -0.0037(6) -0.0136(7) -0.0021(6) O102 0.0224(8) 0.0238(7) 0.0279(8) -0.0056(6) -0.0106(6) -0.0031(6) C101 0.0182(11) 0.0235(9) 0.0227(10) -0.0064(8) -0.0057(8) 0.0026(8) C102 0.0231(11) 0.0202(9) 0.0233(10) -0.0050(8) -0.0012(9) -0.0010(8) C103 0.0177(11) 0.0226(9) 0.0264(11) -0.0072(8) -0.0027(8) -0.0028(8) C104 0.0156(10) 0.0218(9) 0.0211(10) -0.0083(8) -0.0027(8) 0.0017(8) C105 0.0146(10) 0.0187(9) 0.0231(10) -0.0071(8) -0.0024(8) 0.0025(7) C106 0.0160(10) 0.0202(9) 0.0293(11) -0.0092(8) -0.0041(8) -0.0006(8) C107 0.0259(12) 0.0308(11) 0.0308(11) -0.0104(9) -0.0116(10) 0.0003(9) C108 0.0161(11) 0.0228(9) 0.0266(11) -0.0042(8) -0.0046(8) -0.0003(8) C109 0.0282(13) 0.0361(12) 0.0267(11) -0.0048(9) -0.0005(10) -0.0041(10) C110 0.0226(12) 0.0251(10) 0.0372(13) 0.0017(9) -0.0073(10) -0.0012(9) C111 0.0223(12) 0.0275(10) 0.0351(12) -0.0003(9) -0.0057(10) -0.0064(9) O201 0.0226(8) 0.0258(7) 0.0334(8) -0.0120(6) 0.0022(6) -0.0058(6) O202 0.0257(8) 0.0286(7) 0.0279(8) -0.0107(6) 0.0061(6) -0.0053(6) C201 0.0194(11) 0.0241(10) 0.0204(10) -0.0071(8) -0.0052(8) -0.0018(8) C202 0.0222(11) 0.0257(10) 0.0265(11) -0.0134(9) -0.0048(9) 0.0025(8) C203 0.0205(11) 0.0289(10) 0.0227(10) -0.0088(8) -0.0004(8) 0.0018(8) C204 0.0210(11) 0.0253(10) 0.0192(10) -0.0060(8) -0.0036(8) -0.0025(8) C205 0.0193(11) 0.0225(9) 0.0175(9) -0.0062(8) -0.0067(8) 0.0025(8) C206 0.0158(10) 0.0291(10) 0.0184(9) -0.0079(8) -0.0031(8) 0.0022(8) C207 0.0215(12) 0.0327(11) 0.0313(12) -0.0113(9) 0.0016(9) -0.0051(9) C208 0.0230(11) 0.0236(9) 0.0215(10) -0.0077(8) -0.0047(8) 0.0029(8) C209 0.0227(12) 0.0285(10) 0.0284(11) -0.0130(9) -0.0033(9) 0.0056(9) C210 0.0380(14) 0.0282(11) 0.0278(12) -0.0042(9) -0.0029(10) 0.0100(10) C211 0.0280(12) 0.0273(10) 0.0296(11) -0.0112(9) -0.0025(9) -0.0032(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.387(2) . ? O1 C7 1.434(3) . ? O2 C4 1.374(2) . ? C1 C6 1.385(3) . ? C1 C2 1.388(3) . ? C2 C3 1.381(3) . ? C3 C4 1.390(3) . ? C4 C5 1.405(3) . ? C5 C6 1.399(3) . ? C5 C8 1.542(3) . ? C8 C11 1.529(3) . ? C8 C10 1.531(3) . ? C8 C9 1.538(3) . ? O101 C101 1.386(2) . ? O101 C107 1.430(2) . ? O102 C104 1.376(2) . ? C101 C106 1.385(3) . ? C101 C102 1.385(3) . ? C102 C103 1.385(3) . ? C103 C104 1.394(3) . ? C104 C105 1.403(3) . ? C105 C106 1.394(3) . ? C105 C108 1.538(3) . ? C108 C109 1.532(3) . ? C108 C111 1.537(3) . ? C108 C110 1.543(3) . ? O201 C201 1.388(2) . ? O201 C207 1.436(2) . ? O202 C204 1.379(2) . ? C201 C206 1.387(3) . ? C201 C202 1.391(3) . ? C202 C203 1.384(3) . ? C203 C204 1.391(3) . ? C204 C205 1.405(3) . ? C205 C206 1.398(3) . ? C205 C208 1.538(3) . ? C208 C209 1.530(3) . ? C208 C211 1.537(3) . ? C208 C210 1.539(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C7 117.50(16) . . ? O1 C1 C6 123.68(19) . . ? O1 C1 C2 116.25(18) . . ? C6 C1 C2 120.07(19) . . ? C3 C2 C1 118.83(19) . . ? C2 C3 C4 121.18(19) . . ? O2 C4 C3 120.28(18) . . ? O2 C4 C5 118.76(17) . . ? C3 C4 C5 120.95(18) . . ? C6 C5 C4 116.65(18) . . ? C6 C5 C8 121.19(17) . . ? C4 C5 C8 122.15(17) . . ? C1 C6 C5 122.29(19) . . ? C11 C8 C10 107.43(17) . . ? C11 C8 C9 107.33(16) . . ? C10 C8 C9 110.57(17) . . ? C11 C8 C5 111.52(17) . . ? C10 C8 C5 109.50(16) . . ? C9 C8 C5 110.43(17) . . ? C101 O101 C107 117.20(15) . . ? C106 C101 C102 120.24(18) . . ? C106 C101 O101 123.16(18) . . ? C102 C101 O101 116.60(17) . . ? C103 C102 C101 118.74(18) . . ? C102 C103 C104 120.99(18) . . ? O102 C104 C103 119.83(17) . . ? O102 C104 C105 119.34(17) . . ? C103 C104 C105 120.82(18) . . ? C104 C105 C106 116.93(17) . . ? C104 C105 C108 122.07(17) . . ? C106 C105 C108 120.98(17) . . ? C101 C106 C105 122.21(18) . . ? C109 C108 C105 109.27(16) . . ? C109 C108 C111 107.37(17) . . ? C105 C108 C111 111.79(16) . . ? C109 C108 C110 110.41(17) . . ? C105 C108 C110 110.37(17) . . ? C111 C108 C110 107.58(16) . . ? C201 O201 C207 117.27(15) . . ? O201 C201 C206 123.04(18) . . ? O201 C201 C202 116.68(16) . . ? C206 C201 C202 120.26(18) . . ? C203 C202 C201 118.49(17) . . ? C202 C203 C204 121.43(19) . . ? O202 C204 C203 120.49(18) . . ? O202 C204 C205 118.76(16) . . ? C203 C204 C205 120.74(18) . . ? C206 C205 C204 116.97(17) . . ? C206 C205 C208 120.54(18) . . ? C204 C205 C208 122.49(18) . . ? C201 C206 C205 122.09(18) . . ? C209 C208 C211 108.73(16) . . ? C209 C208 C205 111.57(17) . . ? C211 C208 C205 110.02(16) . . ? C209 C208 C210 106.86(17) . . ? C211 C208 C210 110.16(17) . . ? C205 C208 C210 109.44(16) . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.362 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.054 data_tp0509 _database_code_CSD 220678 _audit_creation_method SHELXL-97 _chemical_name_systematic 3-tert-Butyl-4-hydroxyanisole _chemical_name_common BHA _chemical_melting_point '64.8 C' _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 O2' _chemical_formula_weight 180.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 24.2612(11) _cell_length_b 24.2612(11) _cell_length_c 9.3049(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4743.1(5) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10131 _diffrn_reflns_av_R_equivalents 0.0600 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2504 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0895P)^2^+0.7720P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2504 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.09924(4) 0.71119(4) -0.00570(9) 0.0273(2) Uani 1 1 d . . . O2 O 0.08428(4) 0.55242(4) 0.43708(9) 0.0328(3) Uani 1 1 d . . . H1 H 0.0671 0.5134 0.4045 0.039 Uiso 1 1 d R . . C1 C 0.09235(5) 0.66754(5) 0.09897(12) 0.0213(3) Uani 1 1 d . . . C2 C 0.04291(5) 0.60530(5) 0.10399(13) 0.0236(3) Uani 1 1 d . . . H2 H 0.0111 0.5887 0.0315 0.028 Uiso 1 1 calc R . . C3 C 0.04127(5) 0.56764(5) 0.21883(13) 0.0253(3) Uani 1 1 d . . . H3 H 0.0073 0.5249 0.2249 0.030 Uiso 1 1 calc R . . C4 C 0.08759(5) 0.59065(5) 0.32417(12) 0.0234(3) Uani 1 1 d . . . C5 C 0.13838(5) 0.65413(5) 0.32009(12) 0.0211(3) Uani 1 1 d . . . C6 C 0.13881(5) 0.69104(5) 0.20546(12) 0.0209(3) Uani 1 1 d . . . H6 H 0.1722 0.7340 0.1996 0.025 Uiso 1 1 calc R . . C7 C 0.05390(6) 0.68869(6) -0.11935(14) 0.0324(3) Uani 1 1 d . . . H71 H 0.0125 0.6721 -0.0815 0.039 Uiso 1 1 d R . . H72 H 0.0624 0.7201 -0.1816 0.039 Uiso 1 1 d R . . H73 H 0.0504 0.6518 -0.1676 0.039 Uiso 1 1 d R . . C8 C 0.19070(6) 0.68125(5) 0.43500(12) 0.0264(3) Uani 1 1 d . . . C9 C 0.16050(7) 0.67707(6) 0.58304(14) 0.0347(3) Uani 1 1 d . . . H91 H 0.1932 0.6960 0.6489 0.042 Uiso 1 1 d R . . H92 H 0.1333 0.6352 0.6084 0.042 Uiso 1 1 d R . . H93 H 0.1406 0.7025 0.5808 0.042 Uiso 1 1 d R . . C10 C 0.22652(7) 0.64377(7) 0.43465(18) 0.0389(3) Uani 1 1 d . . . H101 H 0.2582(8) 0.6599(8) 0.5111(17) 0.051(5) Uiso 1 1 d . . . H102 H 0.1974(8) 0.5979(8) 0.4516(17) 0.043(4) Uiso 1 1 d . . . H103 H 0.2482(7) 0.6491(8) 0.3380(17) 0.043(4) Uiso 1 1 d . . . C11 C 0.23915(6) 0.75126(6) 0.40701(14) 0.0341(3) Uani 1 1 d . . . H111 H 0.2680 0.7643 0.4805 0.041 Uiso 1 1 d R . . H112 H 0.2196 0.7799 0.4092 0.041 Uiso 1 1 d R . . H113 H 0.2596 0.7558 0.3190 0.041 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0214(4) 0.0287(4) 0.0277(5) 0.0037(3) -0.0067(3) 0.0094(3) O2 0.0448(5) 0.0196(4) 0.0302(5) 0.0034(3) 0.0000(4) 0.0133(4) C1 0.0190(5) 0.0247(6) 0.0228(6) 0.0002(4) 0.0013(4) 0.0129(4) C2 0.0185(5) 0.0252(6) 0.0286(6) -0.0063(5) -0.0019(4) 0.0119(5) C3 0.0208(5) 0.0183(5) 0.0343(7) -0.0030(5) 0.0040(5) 0.0079(4) C4 0.0272(6) 0.0200(5) 0.0249(6) 0.0014(4) 0.0046(5) 0.0133(5) C5 0.0218(5) 0.0210(5) 0.0225(6) -0.0018(4) 0.0010(4) 0.0121(4) C6 0.0173(5) 0.0194(5) 0.0257(6) -0.0004(4) 0.0009(4) 0.0090(4) C7 0.0300(6) 0.0358(7) 0.0276(7) 0.0001(5) -0.0099(5) 0.0135(5) C8 0.0279(6) 0.0244(6) 0.0262(6) 0.0022(5) -0.0060(5) 0.0125(5) C9 0.0453(8) 0.0304(7) 0.0250(7) -0.0004(5) -0.0066(6) 0.0164(6) C10 0.0358(7) 0.0415(8) 0.0461(9) 0.0050(7) -0.0068(7) 0.0244(7) C11 0.0303(6) 0.0299(6) 0.0319(7) 0.0009(5) -0.0131(5) 0.0074(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3860(13) . ? O1 C7 1.4233(14) . ? O2 C4 1.3770(13) . ? C1 C2 1.3821(16) . ? C1 C6 1.3910(15) . ? C2 C3 1.3935(17) . ? C3 C4 1.3813(16) . ? C4 C5 1.4119(16) . ? C5 C6 1.3893(16) . ? C5 C8 1.5338(15) . ? C8 C11 1.5291(17) . ? C8 C9 1.5396(18) . ? C8 C10 1.5402(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C7 117.01(9) . . ? C2 C1 O1 124.46(10) . . ? C2 C1 C6 120.43(10) . . ? O1 C1 C6 115.09(9) . . ? C1 C2 C3 117.84(10) . . ? C4 C3 C2 121.90(10) . . ? O2 C4 C3 120.49(10) . . ? O2 C4 C5 118.71(10) . . ? C3 C4 C5 120.78(10) . . ? C6 C5 C4 116.42(10) . . ? C6 C5 C8 121.38(10) . . ? C4 C5 C8 122.19(10) . . ? C5 C6 C1 122.63(10) . . ? C11 C8 C5 111.67(9) . . ? C11 C8 C9 107.56(10) . . ? C5 C8 C9 109.32(10) . . ? C11 C8 C10 107.95(11) . . ? C5 C8 C10 109.61(10) . . ? C9 C8 C10 110.70(11) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.292 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.042