#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150835.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_7150835
loop_
_publ_author_name
'Flemming, Jonathan P.'
'Berry, Malcolm B.'
'Brown, John M.'
_publ_section_title
;
 Sequential ortho-lithiations; the sulfoxide group as a relay to enable
 meta-substitution
;
_journal_issue                   7
_journal_name_full               'Organic &  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       ω
_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/[A₀*T₀(x)+A₁*T₁(x) ...
+Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed
below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai 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
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
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_occupancy
_atom_site_adp_type
S1 S 0.18404(4) 0.62316(2) 0.76567(2) 0.0162 1.0000 Uani
O1 O 0.33535(11) 0.58947(9) 0.82226(8) 0.0246 1.0000 Uani
C1 C 0.08243(15) 0.48957(10) 0.73136(10) 0.0181 1.0000 Uani
C2 C 0.03745(17) 0.44441(12) 0.84676(12) 0.0255 1.0000 Uani
C3 C 0.19298(16) 0.40972(11) 0.67146(12) 0.0229 1.0000 Uani
C4 C -0.06325(16) 0.51398(11) 0.66187(11) 0.0225 1.0000 Uani
C5 C 0.23041(15) 0.67657(10) 0.62896(10) 0.0168 1.0000 Uani
C6 C 0.11750(15) 0.75020(11) 0.58533(11) 0.0190 1.0000 Uani
C7 C 0.13799(16) 0.79858(12) 0.48062(11) 0.0240 1.0000 Uani
C8 C 0.27396(17) 0.77511(12) 0.42141(11) 0.0250 1.0000 Uani
C9 C 0.38954(16) 0.70735(12) 0.46634(11) 0.0223 1.0000 Uani
C10 C 0.37098(14) 0.65750(10) 0.57060(10) 0.0175 1.0000 Uani
C11 C 0.50846(16) 0.59290(12) 0.61695(11) 0.0232 1.0000 Uani
O2 O 0.58484(12) 0.65282(10) 0.70496(9) 0.0322 1.0000 Uani
O3 O -0.00983(11) 0.76943(9) 0.65152(9) 0.0267 1.0000 Uani
C12 C -0.1194(2) 0.85341(16) 0.61755(16) 0.0426 1.0000 Uani
H1 H 0.502(3) 0.640(2) 0.769(2) 0.075(8) 1.0000 Uiso
H21 H -0.0187 0.3716 0.8381 0.0306 1.0000 Uiso
H22 H -0.0327 0.4992 0.8851 0.0306 1.0000 Uiso
H23 H 0.1345 0.4330 0.8922 0.0306 1.0000 Uiso
H31 H 0.1362 0.3388 0.6539 0.0275 1.0000 Uiso
H32 H 0.2850 0.3930 0.7205 0.0275 1.0000 Uiso
H33 H 0.2304 0.4449 0.6007 0.0275 1.0000 Uiso
H41 H -0.1177 0.4423 0.6435 0.0270 1.0000 Uiso
H42 H -0.1359 0.5632 0.7052 0.0270 1.0000 Uiso
H43 H -0.0318 0.5525 0.5913 0.0270 1.0000 Uiso
H71 H 0.0562 0.8493 0.4488 0.0288 1.0000 Uiso
H81 H 0.2887 0.8075 0.3453 0.0300 1.0000 Uiso
H91 H 0.4882 0.6939 0.4232 0.0268 1.0000 Uiso
H111 H 0.5857 0.5791 0.5557 0.0278 1.0000 Uiso
H112 H 0.4699 0.5199 0.6467 0.0278 1.0000 Uiso
H121 H -0.2062 0.8584 0.6735 0.0512 1.0000 Uiso
H122 H -0.0647 0.9271 0.6124 0.0512 1.0000 Uiso
H123 H -0.1641 0.8334 0.5431 0.0512 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . S1 . C1 . 105.41(6) yes
O1 . S1 . C5 . 108.41(6) yes
C1 . S1 . C5 . 101.85(6) yes
S1 . C1 . C2 . 102.68(9) yes
S1 . C1 . C3 . 110.85(9) yes
C2 . C1 . C3 . 111.02(11) yes
S1 . C1 . C4 . 109.52(9) yes
C2 . C1 . C4 . 110.94(11) yes
C3 . C1 . C4 . 111.50(11) yes
C1 . C2 . H21 . 109.467 no
C1 . C2 . H22 . 109.467 no
H21 . C2 . H22 . 109.476 no
C1 . C2 . H23 . 109.467 no
H21 . C2 . H23 . 109.476 no
H22 . C2 . H23 . 109.476 no
C1 . C3 . H31 . 109.467 no
C1 . C3 . H31 . 109.467 no
C1 . C3 . H32 . 109.467 no
H31 . C3 . H32 . 109.476 no
C1 . C3 . H33 . 109.467 no
H31 . C3 . H33 . 109.476 no
H32 . C3 . H33 . 109.476 no
C1 . C4 . H41 . 109.467 no
C1 . C4 . H42 . 109.467 no
H41 . C4 . H42 . 109.476 no
C1 . C4 . H43 . 109.467 no
H41 . C4 . H43 . 109.475 no
H42 . C4 . H43 . 109.476 no
S1 . C5 . C6 . 114.26(10) yes
S1 . C5 . C10 . 125.57(10) yes
C6 . C5 . C10 . 119.96(12) yes
C5 . C6 . C7 . 120.68(12) yes
C5 . C6 . O3 . 115.69(11) yes
C7 . C6 . O3 . 123.63(12) yes
C6 . C7 . C8 . 118.78(12) yes
C6 . C7 . H71 . 120.610 no
C8 . C7 . H71 . 120.610 no
C7 . C8 . C9 . 120.88(12) yes
C7 . C8 . H81 . 119.562 no
C9 . C8 . H81 . 119.562 no
C8 . C9 . C10 . 121.26(12) yes
C8 . C9 . H91 . 119.371 no
C10 . C9 . H91 . 119.371 no
C5 . C10 . C9 . 118.26(12) yes
C5 . C10 . C11 . 124.11(12) yes
C9 . C10 . C11 . 117.48(12) yes
C10 . C11 . O2 . 111.51(11) yes
C10 . C11 . H111 . 108.959 no
O2 . C11 . H111 . 108.960 no
C10 . C11 . H112 . 108.960 no
O2 . C11 . H112 . 108.960 no
H111 . C11 . H112 . 109.467 no
C11 . O2 . H1 . 99.3(15) no
C6 . O3 . C12 . 118.16(12) yes
O3 . C12 . H121 . 109.467 no
O3 . C12 . H122 . 109.467 no
H121 . C12 . H122 . 109.476 no
O3 . C12 . H123 . 109.467 no
H121 . C12 . H123 . 109.476 no
H122 . C12 . H123 . 109.476 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O1 . 1.5116(10) yes
S1 . C1 . 1.8652(13) yes
S1 . C5 . 1.8038(13) yes
C1 . C2 . 1.5347(18) yes
C1 . C3 . 1.5227(18) yes
C1 . C4 . 1.5232(18) yes
C1 . C4 . 1.5232(18) yes
C2 . H21 . 1.000 no
C2 . H22 . 1.000 no
C2 . H23 . 1.000 no
C3 . H31 . 1.000 no
C3 . H32 . 1.000 no
C3 . H33 . 1.000 no
C4 . H41 . 1.000 no
C4 . H42 . 1.000 no
C4 . H43 . 1.000 no
C5 . C6 . 1.4060(17) yes
C5 . C10 . 1.4060(17) yes
C6 . C7 . 1.3940(18) yes
C6 . O3 . 1.3640(16) yes
C7 . C8 . 1.388(2) yes
C7 . H71 . 1.000 no
C8 . C9 . 1.385(2) yes
C8 . H81 . 1.000 no
C9 . C10 . 1.3948(18) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.5097(18) yes
C11 . O2 . 1.4326(17) yes
C11 . H111 . 1.000 no
C11 . H112 . 1.000 no
O2 . H1 . 1.05(3) no
O3 . C12 . 1.4317(17) yes
C12 . H121 . 1.000 no
C12 . H122 . 1.000 no
C12 . H123 . 1.000 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H1 O1 1.05(3) 154(2) 1.67(3) 2.6597(15) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21118519
2 PubChem 139190239
