#------------------------------------------------------------------------------
#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/95/2009563.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009563
loop_
_publ_author_name
'Raabe, G.'
'Sawicki, M.'
'Frauenrath, H.'
_publ_section_title
;
 trans-2-Phenyltetrahydropyran-3-ylmethyl
 p-toluenesulfonate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              462
_journal_page_last               466
_journal_paper_doi               10.1107/S0108270193008406
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C19 H22 O4 S'
_chemical_formula_weight         346.45
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                98.650(10)
_cell_angle_beta                 98.340(10)
_cell_angle_gamma                101.700(10)
_cell_formula_units_Z            4
_cell_length_a                   9.225(2)
_cell_length_b                   10.141(3)
_cell_length_c                   20.198(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      17.49
_cell_measurement_theta_min      7.91
_cell_volume                     1798.9(8)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.011
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8884
_diffrn_reflns_theta_max         25.3
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.2
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       Irregular
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.3
_refine_diff_density_min         -0.5
_refine_ls_extinction_coef       4925
_refine_ls_extinction_method     'Zachariasen (1963)'
_refine_ls_goodness_of_fit_obs   2.738
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_number_parameters     434
_refine_ls_number_reflns         4657
_refine_ls_R_factor_obs          0.053
_refine_ls_shift/esd_max         '< 0.0005'
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/σ²
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.056
_reflns_number_observed          4657
_reflns_number_total             6495
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sh1064.cif
_cod_data_source_block           sh1064_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=1/\s^2^' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w=1/\s^2^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1798.8
_cod_database_code               2009563
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
S(1) .01090(9) .82374(8) .18880(4) .0541(4)
O(1A) .4137(2) 1.1387(2) .43350(10) .0620(10)
O(2A) .0870(2) .9126(2) .26060(10) .0530(10)
O(3A) -.0789(2) .6985(2) .19810(10) .0700(10)
O(4A) -.0575(2) .9143(2) .15430(10) .0690(10)
C(2A) .3476(3) 1.0511(3) .3691(2) .0510(10)
C(3A) .2085(3) .9463(3) .3774(2) .0540(10)
C(4A) .0956(3) 1.0222(4) .4047(2) .068(2)
C(5A) .1704(4) 1.1244(4) .4681(2) .077(2)
C(6A) .3104(4) 1.2152(4) .4574(2) .073(2)
C(7A) .4664(3) .9856(3) .3436(2) .0500(10)
C(8A) .5029(4) 1.0016(4) .2808(2) .066(2)
C(9A) .6070(4) .9365(5) .2557(2) .082(2)
C(10A) .6737(4) .8555(5) .2921(2) .084(2)
C(11A) .6396(4) .8394(4) .3547(2) .077(2)
C(12A) .5372(4) .9050(4) .3810(2) .063(2)
C(13A) .1410(3) .8421(3) .3140(2) .058(2)
C(14A) .1619(3) .7889(3) .1510(2) .0510(10)
C(15A) .2289(4) .8787(3) .1133(2) .059(2)
C(16A) .3481(4) .8503(4) .0837(2) .065(2)
C(17A) .4018(4) .7352(4) .0924(2) .064(2)
C(18A) .3338(4) .6482(3) .1307(2) .069(2)
C(19A) .2133(4) .6731(3) .1596(2) .062(2)
C(20A) .5343(5) .7074(5) .0619(2) .099(2)
S(2) .40513(9) .70720(9) -.15213(4) .0570(4)
O(1B) .0530(2) .6594(2) -.42080(10) .0650(10)
O(2B) .3397(2) .6888(2) -.23020(10) .0540(10)
O(3B) .4547(3) .5877(2) -.13990(10) .0730(10)
O(4B) .5094(3) .8364(3) -.13700(10) .0800(10)
C(2B) .1007(3) .6655(3) -.3495(2) .0520(10)
C(3B) .1972(3) .5611(3) -.3385(2) .0520(10)
C(4B) .3290(3) .5844(4) -.3766(2) .065(2)
C(5B) .2743(4) .5892(4) -.4504(2) .079(2)
C(6B) .1784(4) .6913(4) -.4545(2) .078(2)
C(7B) -.0397(3) .6400(3) -.3192(2) .053(2)
C(8B) -.0575(4) .7326(4) -.2649(2) .068(2)
C(9B) -.1873(5) .7081(5) -.2365(2) .090(3)
C(10B) -.2975(5) .5928(6) -.2628(3) .097(3)
C(11B) -.2820(4) .4995(4) -.3170(2) .082(2)
C(12B) -.1533(4) .5245(4) -.3454(2) .066(2)
C(13B) .2433(3) .5557(3) -.2646(2) .055(2)
C(14B) .2502(3) .7172(3) -.1124(2) .0510(10)
C(15B) .2047(4) .8389(3) -.1012(2) .065(2)
C(16B) .0793(5) .8434(4) -.0726(2) .075(2)
C(17B) -.0026(4) .7296(5) -.0545(2) .071(2)
C(18B) .0457(4) .6095(4) -.0655(2) .072(2)
C(19B) .1716(4) .6021(3) -.0941(2) .061(2)
C(20B) -.1432(5) .7357(5) -.0262(2) .103(3)
H2A .3153 1.1146 .3356 ?
H3A .2476 .8953 .4130 ?
H41A .0542 1.0717 .3699 ?
H42A .0044 .9510 .4112 ?
H51A .1110 1.1858 .4867 ?
H52A .1954 1.0725 .5077 ?
H61A .3659 1.2861 .4993 ?
H62A .2845 1.2722 .4192 ?
H8A .4533 1.0574 .2519 ?
H9A .6270 .9445 .2101 ?
H10A .7455 .8027 .2764 ?
H11A .6818 .7747 .3825 ?
H12A .5130 .9008 .4289 ?
H131A .2119 .7892 .2949 ?
H132A .0473 .7713 .3198 ?
H15A .1979 .9676 .1050 ?
H16A .3899 .9083 .0511 ?
H18A .3631 .5615 .1327 ?
H19A .1590 .6027 .1873 ?
H201A .5508 .7467 .0259 ?
H202A .5179 .6205 .0315 ?
H203A .6304 .7377 .0947 ?
H2B .1644 .7628 -.3253 ?
H3B .1308 .4682 -.3610 ?
H41B .4036 .6785 -.3525 ?
H42B .3840 .5057 -.3745 ?
H51B .3567 .6013 -.4789 ?
H52B .2133 .4918 -.4753 ?
H61B .1308 .6905 -.5008 ?
H62B .2406 .7990 -.4306 ?
H8B .0290 .8220 -.2441 ?
H9B -.1850 .7919 -.1891 ?
H10B -.3809 .5772 -.2371 ?
H11B -.3597 .4103 -.3426 ?
H12B -.1405 .4537 -.3860 ?
H131B .1565 .5383 -.2407 ?
H132B .2977 .4842 -.2590 ?
H15B .2564 .9225 -.1166 ?
H16B .0462 .9307 -.0605 ?
H18B -.0049 .5237 -.0521 ?
H19B .2009 .5135 -.1059 ?
H201B -.1105 .7988 .0221 ?
H202B -.1560 .6629 -.0003 ?
H203B -.2232 .7619 -.0497 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(3A) S(1) O(4A) 119.90(10) yes
O(3A) S(1) O(2A) 108.70(10) yes
O(3A) S(1) C(14A) 109.10(10) yes
O(4A) S(1) O(2A) 104.10(10) yes
O(4A) S(1) C(14A) 109.6(2) yes
O(2A) S(1) C(14A) 104.40(10) yes
C(2A) O(1A) C(6A) 110.9(2) yes
C(13A) O(2A) S(1) 117.9(2) yes
O(1A) C(2A) C(7A) 108.1(2) yes
O(1A) C(2A) C(3A) 109.4(2) yes
C(7A) C(2A) C(3A) 113.2(3) yes
C(13A) C(3A) C(4A) 113.2(2) yes
C(13A) C(3A) C(2A) 113.0(3) yes
C(4A) C(3A) C(2A) 109.5(3) yes
C(5A) C(4A) C(3A) 110.4(3) yes
C(6A) C(5A) C(4A) 111.2(3) yes
O(1A) C(6A) C(5A) 112.1(3) yes
C(8A) C(7A) C(12A) 118.9(3) yes
C(8A) C(7A) C(2A) 119.9(3) yes
C(12A) C(7A) C(2A) 121.2(3) yes
C(9A) C(8A) C(7A) 120.2(4) yes
C(10A) C(9A) C(8A) 120.5(4) yes
C(9A) C(10A) C(11A) 120.0(4) yes
C(10A) C(11A) C(12A) 120.2(4) yes
C(11A) C(12A) C(7A) 120.2(3) yes
O(2A) C(13A) C(3A) 108.5(3) yes
C(19A) C(14A) C(15A) 120.6(3) yes
C(19A) C(14A) S(1) 119.8(3) yes
C(15A) C(14A) S(1) 119.5(3) yes
C(14A) C(15A) C(16A) 119.1(3) yes
C(17A) C(16A) C(15A) 120.9(3) yes
C(18A) C(17A) C(16A) 118.7(3) yes
C(18A) C(17A) C(20A) 120.7(4) yes
C(16A) C(17A) C(20A) 120.6(4) yes
C(17A) C(18A) C(19A) 121.4(4) yes
C(14A) C(19A) C(18A) 119.2(3) yes
O(3B) S(2) O(4B) 119.90(10) yes
O(3B) S(2) O(2B) 108.90(10) yes
O(3B) S(2) C(14B) 108.7(2) yes
O(4B) S(2) O(2B) 104.10(10) yes
O(4B) S(2) C(14B) 110.00(10) yes
O(2B) S(2) C(14B) 104.20(10) yes
C(6B) O(1B) C(2B) 111.6(2) yes
C(13B) O(2B) S(2) 118.0(2) yes
O(1B) C(2B) C(7B) 106.6(2) yes
O(1B) C(2B) C(3B) 110.1(2) yes
C(7B) C(2B) C(3B) 113.2(3) yes
C(13B) C(3B) C(4B) 113.7(2) yes
C(13B) C(3B) C(2B) 113.0(3) yes
C(4B) C(3B) C(2B) 110.2(3) yes
C(5B) C(4B) C(3B) 110.8(3) yes
C(6B) C(5B) C(4B) 109.9(3) yes
O(1B) C(6B) C(5B) 111.4(3) yes
C(12B) C(7B) C(8B) 118.9(3) yes
C(12B) C(7B) C(2B) 120.6(3) yes
C(8B) C(7B) C(2B) 120.5(3) yes
C(7B) C(8B) C(9B) 120.3(3) yes
C(10B) C(9B) C(8B) 119.7(4) yes
C(9B) C(10B) C(11B) 120.8(4) yes
C(10B) C(11B) C(12B) 119.4(3) yes
C(7B) C(12B) C(11B) 120.8(3) yes
O(2B) C(13B) C(3B) 108.6(2) yes
C(19B) C(14B) C(15B) 120.2(3) yes
C(19B) C(14B) S(2) 119.6(3) yes
C(15B) C(14B) S(2) 120.2(3) yes
C(16B) C(15B) C(14B) 119.4(3) yes
C(15B) C(16B) C(17B) 121.7(4) yes
C(16B) C(17B) C(18B) 117.9(4) yes
C(16B) C(17B) C(20B) 120.6(4) yes
C(18B) C(17B) C(20B) 121.4(4) yes
C(17B) C(18B) C(19B) 121.7(3) yes
C(14B) C(19B) C(18B) 119.1(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) O(3A) 1.423(2) yes
S(1) O(4A) 1.423(3) yes
S(1) O(2A) 1.569(2) yes
S(1) C(14A) 1.754(3) yes
O(1A) C(2A) 1.433(3) yes
O(1A) C(6A) 1.436(5) yes
O(2A) C(13A) 1.465(4) yes
C(2A) H2A 1.055(3) no
C(2A) C(7A) 1.504(5) yes
C(2A) C(3A) 1.538(4) yes
C(3A) H3A 1.013(3) no
C(3A) C(13A) 1.496(4) yes
C(3A) C(4A) 1.531(5) yes
C(4A) H41A .999(4) no
C(4A) H42A 1.030(3) no
C(4A) C(5A) 1.498(5) yes
C(5A) H51A .979(4) no
C(5A) H52A 1.045(4) no
C(5A) C(6A) 1.491(5) yes
C(6A) H61A 1.019(3) no
C(6A) H62A 1.059(4) no
C(7A) C(8A) 1.383(5) yes
C(7A) C(12A) 1.386(5) yes
C(8A) H8A 1.000(4) no
C(8A) C(9A) 1.382(6) yes
C(9A) H9A .978(4) no
C(9A) C(10A) 1.360(7) yes
C(10A) H10A .990(4) no
C(10A) C(11A) 1.372(6) yes
C(11A) H11A 1.024(4) no
C(11A) C(12A) 1.382(6) yes
C(12A) H12A 1.030(3) no
C(13A) H131A 1.009(3) no
C(13A) H132A 1.039(3) no
C(14A) C(19A) 1.377(5) yes
C(14A) C(15A) 1.381(5) yes
C(15A) H15A 1.029(4) no
C(15A) C(16A) 1.384(5) yes
C(16A) H16A 1.015(4) no
C(16A) C(17A) 1.382(6) yes
C(17A) C(18A) 1.375(5) yes
C(17A) C(20A) 1.503(6) yes
C(18A) H18A .975(4) no
C(18A) C(19A) 1.378(5) yes
C(19A) H19A 1.063(4) no
C(20A) H201A .897(5) no
C(20A) H202A .966(4) no
C(20A) H203A .988(4) no
S(2) O(3B) 1.421(3) yes
S(2) O(4B) 1.421(2) yes
S(2) O(2B) 1.572(2) yes
S(2) C(14B) 1.751(3) yes
O(1B) C(6B) 1.431(5) yes
O(1B) C(2B) 1.433(4) yes
O(2B) C(13B) 1.466(3) yes
C(2B) H2B 1.046(3) no
C(2B) C(7B) 1.503(5) yes
C(2B) C(3B) 1.535(5) yes
C(3B) H3B 1.013(3) no
C(3B) C(13B) 1.505(5) yes
C(3B) C(4B) 1.528(5) yes
C(4B) H42B 1.031(4) no
C(4B) H41B 1.058(3) no
C(4B) C(5B) 1.514(5) yes
C(5B) H51B 1.017(4) no
C(5B) H52B 1.043(4) no
C(5B) C(6B) 1.495(6) yes
C(6B) H61B .973(4) no
C(6B) H62B 1.124(4) no
C(7B) C(12B) 1.380(4) yes
C(7B) C(8B) 1.385(5) yes
C(8B) H8B 1.062(3) no
C(8B) C(9B) 1.395(6) yes
C(9B) H9B 1.176(4) no
C(9B) C(10B) 1.363(6) yes
C(10B) H10B .989(5) no
C(10B) C(11B) 1.380(7) yes
C(11B) H11B 1.043(3) no
C(11B) C(12B) 1.386(5) yes
C(12B) H12B 1.043(4) no
C(13B) H132B .973(3) no
C(13B) H131B .993(3) no
C(14B) C(19B) 1.374(5) yes
C(14B) C(15B) 1.380(5) yes
C(15B) H15B 1.001(4) no
C(15B) C(16B) 1.372(6) yes
C(16B) H16B 1.001(4) no
C(16B) C(17B) 1.374(6) yes
C(17B) C(18B) 1.378(6) yes
C(17B) C(20B) 1.500(6) yes
C(18B) H18B .996(4) no
C(18B) C(19B) 1.380(5) yes
C(19B) H19B .995(3) no
C(20B) H203B .926(5) no
C(20B) H202B .965(5) no
C(20B) H201B 1.049(4) no
