Sequential ortho-lithiations; the sulfoxide group as a relay to enable meta-substitution
Flemming, Jonathan P.; Berry, Malcolm B.; Brown, John M.; Organic & Biomolecular Chemistry 6 (2008) 1215–1221; doi:10.1039/B716954j

data_7150835
_publ_section_title
;
 Sequential ortho-lithiations; the sulfoxide group as a relay to enable
 meta-substitution
;
_journal_issue                   7
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              1215
_journal_page_last               1221
_journal_paper_doi               10.1039/B716954j
_journal_volume                  6
_journal_year                    2008
_chemical_compound_source
;
synthesis as described in manuscriptCCDC
;
_chemical_formula_moiety         'C12 H18 O3 S1'
_chemical_formula_sum            'C12 H18 O3 S'
_chemical_formula_weight         242.34
_chemical_melting_point          397.6(15)
_chemical_name_common            2-tert-butylsulfinyl-3-methoxyphenylmethanol
_chemical_name_systematic
;
2-tert-butylsulfinyl-3-methoxyphenylmethanol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.0140(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5196(2)
_cell_length_b                   11.9778(3)
_cell_length_c                   11.9934(3)
_cell_measurement_reflns_used    13716
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     1223.88(5)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor,
1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor,
1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13716
_diffrn_reflns_theta_full        27.458
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         5.357
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
Wed Oct 31 17:30:57 2007 Page 5
enCIFer: arc794.cif

;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       ' fragment '
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0472
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.015332
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin,
1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ...
+A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed
below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
2.85 -0.371 2.02
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0439
_refine_ls_wR_factor_gt          0.0368
_refine_ls_wR_factor_ref         0.0368
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2215
_reflns_number_total             2761
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            B716954j.txt
_cod_data_source_block           arc794
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

'_chemical_melting_point' value '123-6 deg C' was changed to
'397.6(15)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Adriana Da\<skevi\<c, 2011-06-14
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C12 H18 O3 S1'
_cod_database_code               7150835