#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/57/2205797.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_2205797
loop_
_publ_author_name
'Lei Yan'
'Yu-Lin Zhu'
'Yuan-Jiang Pan'
_publ_section_title
4-(o-Methoxyphenyl)-1,3,4,4a,5,6,7,8a-octahydro-2H-pyrano[2,3-d]pyrimidine-2-thione
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1228
_journal_page_last               o1230
_journal_paper_doi               10.1107/S1600536805010068
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H18 N2 O2 S'
_chemical_formula_moiety         'C14 H18 N2 O2 S'
_chemical_formula_sum            'C14 H18 N2 O2 S'
_chemical_formula_weight         278.36
_chemical_name_systematic
;
4-(o-Methoxyphenyl)-1,3,4,4a,5,6,7,8a-octahydro-2H-pyrano[2,3-d]pyrimidin-
2-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.590(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5277(8)
_cell_length_b                   14.2285(13)
_cell_length_c                   11.5972(11)
_cell_measurement_reflns_used    3491
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      2.27
_cell_volume                     1404.4(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8142
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.180
_refine_ls_extinction_coef       0.047(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0509P)²+0.1006P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                2486
_reflns_number_total             3056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg6001.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/c'
_cod_database_code               2205797
_cod_database_fobs_code          2205797
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S 0.25941(4) 1.03808(2) 0.50902(3) 0.04922(13) Uani d . 1 S
O 0.52757(12) 0.62301(7) 0.32986(8) 0.0554(3) Uani d . 1 O
O8 0.05112(11) 0.78727(6) 0.28608(8) 0.0501(2) Uani d . 1 O
N1 0.09723(12) 0.88751(7) 0.44083(10) 0.0486(3) Uani d . 1 N
H1 0.0176 0.9243 0.4438 0.058 Uiso calc R 1 H
N3 0.36430(11) 0.86875(7) 0.45926(9) 0.0420(3) Uani d . 1 N
H3 0.4553 0.8935 0.4741 0.050 Uiso calc R 1 H
C2 0.24014(13) 0.92390(8) 0.46682(11) 0.0387(3) Uani d . 1 C
C4 0.35904(13) 0.76851(8) 0.42744(11) 0.0369(3) Uani d . 1 C
H4 0.3701 0.7624 0.3442 0.044 Uiso calc R 1 H
C5 0.17041(17) 0.62802(9) 0.41244(13) 0.0529(4) Uani d . 1 C
H5A 0.2632 0.5903 0.4313 0.064 Uiso calc R 1 H
H5B 0.0839 0.6007 0.4514 0.064 Uiso calc R 1 H
C6 0.13230(19) 0.62462(11) 0.28285(14) 0.0623(4) Uani d . 1 C
H6A 0.2258 0.6390 0.2428 0.075 Uiso calc R 1 H
H6B 0.0978 0.5619 0.2605 0.075 Uiso calc R 1 H
C7 0.00511(18) 0.69443(11) 0.24897(14) 0.0576(4) Uani d . 1 C
H7A -0.0152 0.6938 0.1657 0.069 Uiso calc R 1 H
H7B -0.0910 0.6768 0.2839 0.069 Uiso calc R 1 H
C9 0.06775(14) 0.79185(9) 0.40848(11) 0.0414(3) Uani d . 1 C
H9 -0.0310 0.7718 0.4397 0.050 Uiso calc R 1 H
C10 0.19946(14) 0.72839(8) 0.45717(11) 0.0399(3) Uani d . 1 C
H10 0.1961 0.7275 0.5415 0.048 Uiso calc R 1 H
C11 0.49464(14) 0.71785(8) 0.49245(11) 0.0379(3) Uani d . 1 C
C12 0.57727(14) 0.64627(8) 0.44041(11) 0.0410(3) Uani d . 1 C
C13 0.70307(16) 0.60268(9) 0.50094(13) 0.0505(3) Uani d . 1 C
H13 0.7608 0.5570 0.4650 0.061 Uiso calc R 1 H
C14 0.74240(17) 0.62693(10) 0.61368(15) 0.0601(4) Uani d . 1 C
H14 0.8268 0.5976 0.6536 0.072 Uiso calc R 1 H
C15 0.65802(17) 0.69419(10) 0.66778(13) 0.0571(4) Uani d . 1 C
H15 0.6827 0.7091 0.7449 0.069 Uiso calc R 1 H
C16 0.53596(16) 0.73958(9) 0.60660(12) 0.0467(3) Uani d . 1 C
H16 0.4802 0.7859 0.6431 0.056 Uiso calc R 1 H
C17 0.5777(2) 0.53592(11) 0.28420(15) 0.0640(4) Uani d . 1 C
H17A 0.6868 0.5400 0.2689 0.077 Uiso calc R 1 H
H17B 0.5169 0.5223 0.2137 0.077 Uiso calc R 1 H
H17C 0.5632 0.4867 0.3392 0.077 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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
C12 O C17 118.51(11) y
C9 O8 C7 110.51(10) ?
C2 N1 C9 124.67(10) ?
C2 N1 H1 117.7 ?
C9 N1 H1 117.7 ?
C2 N3 C4 125.30(10) y
C2 N3 H3 117.3 ?
C4 N3 H3 117.3 ?
N3 C2 N1 118.37(11) y
N3 C2 S 121.41(9) ?
N1 C2 S 120.22(9) ?
N3 C4 C11 108.92(10) ?
N3 C4 C10 108.50(9) ?
C11 C4 C10 111.68(10) ?
N3 C4 H4 109.2 ?
C11 C4 H4 109.2 ?
C10 C4 H4 109.2 ?
C6 C5 C10 112.61(11) ?
C6 C5 H5A 109.1 ?
C10 C5 H5A 109.1 ?
C6 C5 H5B 109.1 ?
C10 C5 H5B 109.1 ?
H5A C5 H5B 107.8 ?
C7 C6 C5 110.09(12) ?
C7 C6 H6A 109.6 ?
C5 C6 H6A 109.6 ?
C7 C6 H6B 109.6 ?
C5 C6 H6B 109.6 ?
H6A C6 H6B 108.2 ?
O8 C7 C6 110.48(11) ?
O8 C7 H7A 109.6 ?
C6 C7 H7A 109.6 ?
O8 C7 H7B 109.6 ?
C6 C7 H7B 109.6 ?
H7A C7 H7B 108.1 ?
O8 C9 N1 108.13(10) ?
O8 C9 C10 111.65(10) y
N1 C9 C10 110.72(10) ?
O8 C9 H9 108.8 ?
N1 C9 H9 108.8 ?
C10 C9 H9 108.8 ?
C9 C10 C5 109.09(10) ?
C9 C10 C4 109.89(10) ?
C5 C10 C4 113.39(10) ?
C9 C10 H10 108.1 ?
C5 C10 H10 108.1 ?
C4 C10 H10 108.1 ?
C16 C11 C12 118.11(11) ?
C16 C11 C4 120.55(11) ?
C12 C11 C4 121.30(11) ?
O C12 C13 123.37(11) y
O C12 C11 116.55(11) y
C13 C12 C11 120.07(12) ?
C14 C13 C12 120.22(13) ?
C14 C13 H13 119.9 ?
C12 C13 H13 119.9 ?
C15 C14 C13 120.43(13) ?
C15 C14 H14 119.8 ?
C13 C14 H14 119.8 ?
C14 C15 C16 119.38(14) ?
C14 C15 H15 120.3 ?
C16 C15 H15 120.3 ?
C15 C16 C11 121.68(13) ?
C15 C16 H16 119.2 ?
C11 C16 H16 119.2 ?
O C17 H17A 109.5 ?
O C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C2 1.7018(12) y
O C12 1.3655(15) y
O C17 1.4238(16) ?
O8 C9 1.4191(16) ?
O8 C7 1.4363(17) ?
N1 C2 1.3409(15) y
N1 C9 1.4299(15) y
N1 H1 0.8600 ?
N3 C2 1.3251(14) y
N3 C4 1.4733(15) y
N3 H3 0.8600 ?
C4 C11 1.5218(16) ?
C4 C10 1.5347(17) ?
C4 H4 0.9800 ?
C5 C6 1.518(2) ?
C5 C10 1.5342(17) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C7 1.505(2) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C9 C10 1.5220(17) ?
C9 H9 0.9800 ?
C10 H10 0.9800 ?
C11 C16 1.3835(18) ?
C11 C12 1.3970(17) ?
C12 C13 1.3906(17) ?
C13 C14 1.373(2) ?
C13 H13 0.9300 ?
C14 C15 1.373(2) ?
C14 H14 0.9300 ?
C15 C16 1.3825(18) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
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
_geom_hbond_publ_flag
N1 H1 S 3_576 0.86 2.52 3.3061(11) 153 yes
N3 H3 S 3_676 0.86 2.62 3.4702(11) 172 yes
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
_geom_torsion_publ_flag
C4 N3 C2 N1 -1.86(19) ?
C4 N3 C2 S 177.82(9) ?
C9 N1 C2 N3 1.98(19) ?
C9 N1 C2 S -177.71(10) ?
C2 N3 C4 C11 -146.77(12) ?
C2 N3 C4 C10 -25.00(16) ?
C10 C5 C6 C7 -49.79(16) ?
C9 O8 C7 C6 -64.43(15) ?
C5 C6 C7 O8 56.65(17) ?
C7 O8 C9 N1 -174.01(10) ?
C7 O8 C9 C10 63.95(13) ?
C2 N1 C9 O8 -97.21(14) ?
C2 N1 C9 C10 25.40(17) ?
O8 C9 C10 C5 -54.86(14) y
N1 C9 C10 C5 -175.40(11) ?
O8 C9 C10 C4 70.02(13) y
N1 C9 C10 C4 -50.52(14) ?
C6 C5 C10 C9 48.22(15) ?
C6 C5 C10 C4 -74.58(14) ?
N3 C4 C10 C9 49.50(13) ?
C11 C4 C10 C9 169.56(10) y
N3 C4 C10 C5 171.86(10) ?
C11 C4 C10 C5 -68.08(14) y
N3 C4 C11 C16 40.14(15) ?
C10 C4 C11 C16 -79.68(14) ?
N3 C4 C11 C12 -142.05(11) ?
C10 C4 C11 C12 98.13(13) ?
C17 O C12 C13 16.64(19) ?
C17 O C12 C11 -163.39(12) ?
C16 C11 C12 O 176.37(11) ?
C4 C11 C12 O -1.49(17) ?
C16 C11 C12 C13 -3.65(19) ?
C4 C11 C12 C13 178.48(11) ?
O C12 C13 C14 -177.22(13) ?
C11 C12 C13 C14 2.8(2) ?
C12 C13 C14 C15 0.1(2) ?
C13 C14 C15 C16 -2.0(2) ?
C14 C15 C16 C11 1.1(2) ?
C12 C11 C16 C15 1.72(19) ?
C4 C11 C16 C15 179.60(13) ?
