#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204865.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_2204865
loop_
_publ_author_name
'Hartung, Jens'
'Svoboda, Ingrid'
'Schmidt, Philipp'
'Murso, Alexander'
_publ_section_title
;
 <i>trans</i>-2,2-Dimethyl-6-phenyl-3,4,5,6-tetrahydro-2<i>H</i>-pyran-3-ol
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o33
_journal_page_last               o34
_journal_paper_doi               10.1107/S1600536804031551
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C13 H18 O2'
_chemical_formula_moiety         'C13 H18 O2'
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_chemical_name_common
;
trans-2,2-Dimethyl-6-phenyltetrahydropyran-3-ol
;
_chemical_name_systematic
;
trans-2,2-Dimethyl-6-phenyl-3,4,5,6-tetrahydro-2H-pyran-3-ol
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.6090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4212(6)
_cell_length_b                   12.8792(9)
_cell_length_c                   10.0568(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      14.84
_cell_measurement_theta_min      3.25
_cell_volume                     1175.26(14)
_computing_cell_refinement
;
CAD-4 Diffractometer Control Software
;
_computing_data_collection
;
CAD-4 Diffractometer Control Software (Enraf--Nonius, 1993)
;
_computing_data_reduction
;
CAD-4 Diffractometer Control Software
;
_computing_molecular_graphics
;
PLATON (Spek, 2002) and ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2148
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.8889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                2056
_reflns_number_total             2148
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cv6413.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204865
_cod_database_fobs_code          2204865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_type_symbol
C2 0.2568(2) 0.25944(17) 0.7167(2) 0.0259(5) Uani d . 1 C
C3 0.4194(2) 0.24944(19) 0.7962(2) 0.0307(5) Uani d . 1 C
H3 0.4775 0.2986 0.7545 0.037 Uiso calc R 1 H
C4 0.4791(3) 0.1413(2) 0.7891(2) 0.0362(6) Uani d . 1 C
H4A 0.4303 0.0923 0.8385 0.043 Uiso calc R 1 H
H4B 0.5862 0.1403 0.8349 0.043 Uiso calc R 1 H
C5 0.4519(3) 0.1067(2) 0.6385(2) 0.0354(6) Uani d . 1 C
H5A 0.5108 0.1503 0.5920 0.042 Uiso calc R 1 H
H5B 0.4834 0.0337 0.6353 0.042 Uiso calc R 1 H
C6 0.2884(2) 0.11692(17) 0.5633(2) 0.0290(5) Uani d . 1 C
H1 0.2308 0.0676 0.6054 0.035 Uiso calc R 1 H
C7 0.1543(2) 0.2004(2) 0.7847(2) 0.0348(6) Uani d . 1 C
H7A 0.0531 0.2040 0.7254 0.052 Uiso calc R 1 H
H7B 0.1586 0.2317 0.8745 0.052 Uiso calc R 1 H
H7C 0.1854 0.1277 0.7977 0.052 Uiso calc R 1 H
C8 0.2113(3) 0.3727(2) 0.6974(3) 0.0421(6) Uani d . 1 C
H8A 0.2758 0.4092 0.6511 0.063 Uiso calc R 1 H
H8B 0.2199 0.4045 0.7878 0.063 Uiso calc R 1 H
H8C 0.1090 0.3774 0.6410 0.063 Uiso calc R 1 H
C9 0.2549(2) 0.09506(17) 0.4100(2) 0.0273(5) Uani d . 1 C
C10 0.3018(3) 0.16225(19) 0.3222(2) 0.0349(6) Uani d . 1 C
H10 0.3548 0.2232 0.3589 0.042 Uiso calc R 1 H
C11 0.2727(3) 0.1421(2) 0.1829(3) 0.0407(6) Uani d . 1 C
H11 0.3050 0.1891 0.1243 0.049 Uiso calc R 1 H
C12 0.1967(3) 0.0538(2) 0.1289(3) 0.0418(6) Uani d . 1 C
H12 0.1769 0.0397 0.0330 0.050 Uiso calc R 1 H
C13 0.1490(3) -0.0142(2) 0.2133(3) 0.0406(6) Uani d . 1 C
H13 0.0964 -0.0751 0.1755 0.049 Uiso calc R 1 H
C14 0.1779(2) 0.00613(19) 0.3545(2) 0.0338(5) Uani d . 1 C
H14 0.1449 -0.0408 0.4127 0.041 Uiso calc R 1 H
O1 0.23850(15) 0.22124(11) 0.57643(14) 0.0267(4) Uani d . 1 O
O2 0.43287(19) 0.28157(14) 0.93511(16) 0.0359(4) Uani d . 1 O
H2 0.523(3) 0.279(2) 0.974(3) 0.046(8) Uiso d . 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C2 0.0280(11) 0.0283(12) 0.0196(11) 0.0012(9) 0.0033(8) -0.0028(9)
C3 0.0260(11) 0.0415(13) 0.0223(11) -0.0035(10) 0.0024(9) -0.0033(10)
C4 0.0285(12) 0.0460(15) 0.0290(12) 0.0069(11) -0.0008(9) 0.0010(11)
C5 0.0309(12) 0.0396(14) 0.0331(13) 0.0103(10) 0.0041(10) -0.0021(10)
C6 0.0316(12) 0.0263(12) 0.0282(12) 0.0013(9) 0.0066(9) 0.0013(9)
C7 0.0281(11) 0.0517(15) 0.0242(11) -0.0008(11) 0.0061(9) -0.0014(11)
C8 0.0526(16) 0.0358(14) 0.0317(13) 0.0072(12) 0.0005(11) -0.0050(11)
C9 0.0237(11) 0.0304(12) 0.0269(11) 0.0066(9) 0.0052(9) -0.0010(9)
C10 0.0331(12) 0.0365(13) 0.0349(13) -0.0076(10) 0.0087(10) -0.0027(10)
C11 0.0412(14) 0.0510(16) 0.0323(13) -0.0050(12) 0.0140(11) 0.0047(11)
C12 0.0416(14) 0.0592(17) 0.0247(12) 0.0020(13) 0.0091(10) -0.0076(12)
C13 0.0406(14) 0.0367(14) 0.0414(14) -0.0069(11) 0.0057(11) -0.0137(11)
C14 0.0338(12) 0.0307(13) 0.0387(13) 0.0006(10) 0.0126(10) 0.0033(10)
O1 0.0285(8) 0.0278(8) 0.0211(8) 0.0037(6) 0.0020(6) -0.0016(6)
O2 0.0285(9) 0.0521(11) 0.0236(8) -0.0018(8) 0.0008(7) -0.0067(7)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C2 C8 104.14(17)
O1 C2 C7 109.89(17)
C8 C2 C7 110.2(2)
O1 C2 C3 108.49(16)
C8 C2 C3 110.85(19)
C7 C2 C3 112.92(18)
O2 C3 C4 112.13(19)
O2 C3 C2 107.37(17)
C4 C3 C2 112.68(19)
O2 C3 H3 108.2
C4 C3 H3 108.2
C2 C3 H3 108.2
C3 C4 C5 110.41(19)
C3 C4 H4A 109.6
C5 C4 H4A 109.6
C3 C4 H4B 109.6
C5 C4 H4B 109.6
H4A C4 H4B 108.1
C6 C5 C4 110.04(19)
C6 C5 H5A 109.7
C4 C5 H5A 109.7
C6 C5 H5B 109.7
C4 C5 H5B 109.7
H5A C5 H5B 108.2
O1 C6 C9 106.45(17)
O1 C6 C5 110.16(18)
C9 C6 C5 113.21(18)
O1 C6 H1 109.0
C9 C6 H1 109.0
C5 C6 H1 109.0
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C2 C8 H8A 109.5
C2 C8 H8B 109.5
H8A C8 H8B 109.5
C2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C14 C9 C10 118.6(2)
C14 C9 C6 120.3(2)
C10 C9 C6 121.1(2)
C11 C10 C9 121.2(2)
C11 C10 H10 119.4
C9 C10 H10 119.4
C12 C11 C10 119.8(2)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 120.3(2)
C11 C12 H12 119.8
C13 C12 H12 119.8
C12 C13 C14 120.0(2)
C12 C13 H13 120.0
C14 C13 H13 120.0
C9 C14 C13 120.0(2)
C9 C14 H14 120.0
C13 C14 H14 120.0
C6 O1 C2 116.51(15)
C3 O2 H2 104.8(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O1 1.460(2)
C2 C8 1.517(3)
C2 C7 1.527(3)
C2 C3 1.531(3)
C3 O2 1.430(3)
C3 C4 1.511(3)
C3 H3 1.0000
C4 C5 1.532(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.528(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 O1 1.441(3)
C6 C9 1.514(3)
C6 H1 1.0000
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C14 1.390(3)
C9 C10 1.390(3)
C10 C11 1.378(3)
C10 H10 0.9500
C11 C12 1.375(4)
C11 H11 0.9500
C12 C13 1.377(4)
C12 H12 0.9500
C13 C14 1.397(3)
C13 H13 0.9500
C14 H14 0.9500
O2 H2 0.83(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2 O1 4_666 0.83(3) 2.02(3) 2.848(2) 177(3)
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
O1 C2 C3 O2 -176.68(17)
C8 C2 C3 O2 69.6(2)
C7 C2 C3 O2 -54.6(2)
O1 C2 C3 C4 -52.7(2)
C8 C2 C3 C4 -166.5(2)
C7 C2 C3 C4 69.3(2)
O2 C3 C4 C5 175.67(19)
C2 C3 C4 C5 54.4(3)
C3 C4 C5 C6 -54.3(3)
C4 C5 C6 O1 54.9(3)
C4 C5 C6 C9 173.9(2)
O1 C6 C9 C14 -128.4(2)
C5 C6 C9 C14 110.4(2)
O1 C6 C9 C10 52.4(3)
C5 C6 C9 C10 -68.7(3)
C14 C9 C10 C11 0.2(3)
C6 C9 C10 C11 179.4(2)
C9 C10 C11 C12 -0.4(4)
C10 C11 C12 C13 0.3(4)
C11 C12 C13 C14 -0.1(4)
C10 C9 C14 C13 0.0(3)
C6 C9 C14 C13 -179.2(2)
C12 C13 C14 C9 0.0(4)
C9 C6 O1 C2 178.85(16)
C5 C6 O1 C2 -58.0(2)
C8 C2 O1 C6 173.88(18)
C7 C2 O1 C6 -68.1(2)
C3 C2 O1 C6 55.8(2)