#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/16/2201636.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_2201636
loop_
_publ_author_name
'Rickard, Clifton E. F.'
'Brimble, Margaret A.'
'Pavia, Gabrielle'
'Stevenson, Ralph J.'
_publ_section_title
;
 cis-2-(2-Methoxyphenyl)-3-(phenylselenyl)tetrahydropyran
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o933
_journal_page_last               o934
_journal_paper_doi               10.1107/S1600536802013272
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C18 H20 O2 Se'
_chemical_formula_moiety         'C18 H20 O2 Se'
_chemical_formula_sum            'C18 H20 O2 Se'
_chemical_formula_weight         347.30
_chemical_name_systematic
;
cis-2-(2-Methoxyphenyl)-3-(phenylselenyl)tetrahydropyran
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.180(2)
_cell_angle_beta                 97.654(2)
_cell_angle_gamma                94.793(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1823(4)
_cell_length_b                   7.7739(4)
_cell_length_c                   13.9367(7)
_cell_measurement_reflns_used    6450
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     761.18(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT  (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 Sheldrick, (1997)'
_computing_structure_solution    'SHELXS Sheldrick, (1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Siemens SMART'
_diffrn_measurement_method       'Area-detector ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.021
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7048
_diffrn_reflns_theta_full        26.1
_diffrn_reflns_theta_max         26.1
_diffrn_reflns_theta_min         1.5
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.468
_exptl_absorpt_correction_T_max  0.709
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular fragment'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.020
_refine_ls_R_factor_gt           0.019
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0303P)²+0.2068P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.051
_refine_ls_wR_factor_ref         0.052
_reflns_number_gt                2832
_reflns_number_total             2984
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6071.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2201636
_cod_database_fobs_code          2201636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_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
Se 0.06350(2) 0.534651(18) 0.203666(10) 0.01788(6) Uani d . 1 . . Se
O1 -0.07940(15) 0.91423(15) 0.24290(8) 0.0206(2) Uani d . 1 . . O
C2 0.0635(2) 0.87059(19) 0.31477(10) 0.0165(3) Uani d . 1 . . C
H2 0.1363 0.9820 0.3483 0.020 Uiso calc R 1 . . H
C3 0.2028(2) 0.76066(19) 0.26609(10) 0.0162(3) Uani d . 1 . . C
H3 0.3053 0.7383 0.3176 0.019 Uiso calc R 1 . . H
C4 0.2906(2) 0.8619(2) 0.19316(11) 0.0205(3) Uani d . 1 . . C
H4 0.3739(12) 0.9581(13) 0.2280(5) 0.025 Uiso calc R 1 . . H
H4A 0.3632(11) 0.7879(10) 0.1566(5) 0.025 Uiso calc R 1 . . H
C5 0.1403(2) 0.9289(2) 0.12311(11) 0.0233(3) Uani d . 1 . . C
H5 0.2008(9) 1.0089(11) 0.0853(6) 0.028 Uiso calc R 1 . . H
H5A 0.0724(10) 0.8313(14) 0.0776(7) 0.028 Uiso calc R 1 . . H
C6 0.0020(3) 1.0220(2) 0.17917(12) 0.0256(3) Uani d . 1 . . C
H6 0.0678(10) 1.1294(16) 0.2183(6) 0.031 Uiso calc R 1 . . H
H6A -0.0995(15) 1.0553(6) 0.1325(7) 0.031 Uiso calc R 1 . . H
O2 0.25985(15) 0.84935(15) 0.49284(8) 0.0226(2) Uani d . 1 . . O
C1' 0.0743(2) 0.78189(19) 0.48253(10) 0.0174(3) Uani d . 1 . . C
C2' -0.0311(2) 0.78706(19) 0.39071(10) 0.0165(3) Uani d . 1 . . C
C3' -0.2203(2) 0.7213(2) 0.37402(11) 0.0199(3) Uani d . 1 . . C
H3B -0.2931 0.7237 0.3122 0.024 Uiso calc R 1 . . H
C4' -0.3043(2) 0.6516(2) 0.44729(12) 0.0231(3) Uani d . 1 . . C
H4B -0.4339 0.6076 0.4354 0.028 Uiso calc R 1 . . H
C5' -0.1986(2) 0.6468(2) 0.53695(11) 0.0231(3) Uani d . 1 . . C
H5B -0.2559 0.5989 0.5866 0.028 Uiso calc R 1 . . H
C6' -0.0087(2) 0.7113(2) 0.55539(11) 0.0206(3) Uani d . 1 . . C
H6B 0.0636 0.7072 0.6172 0.025 Uiso calc R 1 . . H
C7' 0.3694(2) 0.8605(2) 0.58719(11) 0.0250(3) Uani d . 1 . . C
H7A 0.3083 0.9292 0.6356 0.038 Uiso calc R 1 . . H
H7B 0.4961 0.9168 0.5860 0.038 Uiso calc R 1 . . H
H7C 0.3789 0.7430 0.6048 0.038 Uiso calc R 1 . . H
C1" 0.2638(2) 0.43192(19) 0.14563(11) 0.0171(3) Uani d . 1 . . C
C2" 0.2418(2) 0.3869(2) 0.04492(11) 0.0212(3) Uani d . 1 . . C
H2C 0.1343 0.4169 0.0054 0.025 Uiso calc R 1 . . H
C3" 0.3760(3) 0.2982(2) 0.00151(12) 0.0261(4) Uani d . 1 . . C
H3C 0.3584 0.2655 -0.0673 0.031 Uiso calc R 1 . . H
C4" 0.5356(2) 0.2573(2) 0.05848(12) 0.0272(4) Uani d . 1 . . C
H4C 0.6274 0.1967 0.0289 0.033 Uiso calc R 1 . . H
C5" 0.5600(2) 0.3058(2) 0.15928(12) 0.0270(4) Uani d . 1 . . C
H5C 0.6703 0.2804 0.1985 0.032 Uiso calc R 1 . . H
C6" 0.4247(2) 0.3907(2) 0.20269(11) 0.0231(3) Uani d . 1 . . C
H6C 0.4411 0.4212 0.2717 0.028 Uiso calc R 1 . . H
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1" Se C3 99.14(6) y
C2 O1 C6 110.71(12) y
O1 C2 C2' 108.62(12) y
O1 C2 C3 110.67(11) y
C2' C2 C3 114.91(12) y
O1 C2 H2 107.4 ?
C2' C2 H2 107.4 ?
C3 C2 H2 107.4 ?
C4 C3 C2 109.31(12) y
C4 C3 Se 112.70(10) y
C2 C3 Se 108.13(10) y
C4 C3 H3 108.9 ?
C2 C3 H3 108.9 ?
Se C3 H3 108.9 ?
C5 C4 C3 111.69(13) y
C5 C4 H4 109.3 ?
C3 C4 H4 109.3 ?
C5 C4 H4A 109.3 ?
C3 C4 H4A 109.3 ?
H4 C4 H4A 107.9 ?
C6 C5 C4 110.60(13) y
C6 C5 H5 109.5 ?
C4 C5 H5 109.5 ?
C6 C5 H5A 109.5 ?
C4 C5 H5A 109.5 ?
H5 C5 H5A 108.1 ?
O1 C6 C5 111.84(13) y
O1 C6 H6 109.2 ?
C5 C6 H6 109.2 ?
O1 C6 H6A 109.2 ?
C5 C6 H6A 109.2 ?
H6 C6 H6A 107.9 ?
C1' O2 C7' 117.40(12) ?
O2 C1' C6' 124.24(14) ?
O2 C1' C2' 115.11(13) ?
C6' C1' C2' 120.65(14) ?
C3' C2' C1' 118.86(14) ?
C3' C2' C2 122.35(13) ?
C1' C2' C2 118.74(13) ?
C2' C3' C4' 120.61(15) ?
C2' C3' H3B 119.7 ?
C4' C3' H3B 119.7 ?
C5' C4' C3' 119.80(15) ?
C5' C4' H4B 120.1 ?
C3' C4' H4B 120.1 ?
C4' C5' C6' 120.70(14) ?
C4' C5' H5B 119.6 ?
C6' C5' H5B 119.6 ?
C1' C6' C5' 119.37(14) ?
C1' C6' H6B 120.3 ?
C5' C6' H6B 120.3 ?
O2 C7' H7A 109.5 ?
O2 C7' H7B 109.5 ?
H7A C7' H7B 109.5 ?
O2 C7' H7C 109.5 ?
H7A C7' H7C 109.5 ?
H7B C7' H7C 109.5 ?
C2" C1" C6" 119.23(14) ?
C2" C1" Se 118.99(12) ?
C6" C1" Se 121.63(11) ?
C1" C2" C3" 120.40(15) ?
C1" C2" H2C 119.8 ?
C3" C2" H2C 119.8 ?
C4" C3" C2" 120.18(15) ?
C4" C3" H3C 119.9 ?
C2" C3" H3C 119.9 ?
C3" C4" C5" 119.49(15) ?
C3" C4" H4C 120.3 ?
C5" C4" H4C 120.3 ?
C6" C5" C4" 120.35(15) ?
C6" C5" H5C 119.8 ?
C4" C5" H5C 119.8 ?
C5" C6" C1" 120.32(14) ?
C5" C6" H6C 119.8 ?
C1" C6" H6C 119.8 ?
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
Se C1" . 1.9244(15) y
Se C3 . 1.9842(15) y
O1 C2 . 1.4289(18) y
O1 C6 . 1.4405(18) y
C2 C2' . 1.5145(19) y
C2 C3 . 1.539(2) y
C2 H2 . 1.0000 ?
C3 C4 . 1.529(2) y
C3 H3 . 1.0000 ?
C4 C5 . 1.526(2) y
C4 H4 . 0.9536 ?
C4 H4A . 0.9536 ?
C5 C6 . 1.519(2) y
C5 H5 . 0.9754 ?
C5 H5A . 0.9754 ?
C6 H6 . 0.9844 ?
C6 H6A . 0.9844 ?
O2 C1' . 1.3731(18) ?
O2 C7' . 1.4284(18) ?
C1' C6' . 1.390(2) ?
C1' C2' . 1.404(2) ?
C2' C3' . 1.390(2) ?
C3' C4' . 1.396(2) ?
C3' H3B . 0.9500 ?
C4' C5' . 1.380(2) ?
C4' H4B . 0.9500 ?
C5' C6' . 1.392(2) ?
C5' H5B . 0.9500 ?
C6' H6B . 0.9500 ?
C7' H7A . 0.9800 ?
C7' H7B . 0.9800 ?
C7' H7C . 0.9800 ?
C1" C2" . 1.388(2) ?
C1" C6" . 1.396(2) ?
C2" C3" . 1.390(2) ?
C2" H2C . 0.9500 ?
C3" C4" . 1.388(3) ?
C3" H3C . 0.9500 ?
C4" C5" . 1.392(2) ?
C4" H4C . 0.9500 ?
C5" C6" . 1.382(2) ?
C5" H5C . 0.9500 ?
C6" H6C . 0.9500 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 O1 C2 C2' 169.53(12)
C6 O1 C2 C3 -63.46(15)
O1 C2 C3 C4 57.78(15)
C2' C2 C3 C4 -178.76(12)
O1 C2 C3 Se -65.24(13)
C2' C2 C3 Se 58.22(14)
C1" Se C3 C4 56.72(11)
C1" Se C3 C2 177.66(10)
C2 C3 C4 C5 -50.98(16)
Se C3 C4 C5 69.28(14)
C3 C4 C5 C6 49.53(18)
C2 O1 C6 C5 61.79(17)
C4 C5 C6 O1 -54.16(19)
C7' O2 C1' C6' -5.4(2)
C7' O2 C1' C2' 174.98(13)
O2 C1' C2' C3' 179.95(13)
C6' C1' C2' C3' 0.4(2)
O2 C1' C2' C2 -2.41(19)
C6' C1' C2' C2 177.99(14)
O1 C2 C2' C3' 16.94(19)
C3 C2 C2' C3' -107.61(16)
O1 C2 C2' C1' -160.62(12)
C3 C2 C2' C1' 74.84(17)
C1' C2' C3' C4' 0.1(2)
C2 C2' C3' C4' -177.41(14)
C2' C3' C4' C5' -0.4(2)
C3' C4' C5' C6' 0.2(2)
O2 C1' C6' C5' 179.88(14)
C2' C1' C6' C5' -0.6(2)
C4' C5' C6' C1' 0.3(2)
C3 Se C1" C2" -119.70(13)
C3 Se C1" C6" 64.77(14)
C6" C1" C2" C3" 1.5(2)
Se C1" C2" C3" -174.13(13)
C1" C2" C3" C4" -1.5(3)
C2" C3" C4" C5" 0.0(3)
C3" C4" C5" C6" 1.4(3)
C4" C5" C6" C1" -1.3(3)
C2" C1" C6" C5" -0.1(2)
Se C1" C6" C5" 175.40(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139065560
