#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:52:34 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153465.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_7153465
loop_
_publ_author_name
'Sakamoto, Masami'
'Yagishita, Fumitoshi'
'Ando, Masaru'
'Sasahara, Yuich'
'Kamataki, Norifumi'
'Ohta, Mai'
'Mino, Takashi'
'Kasashima, Yoshio'
'Fujita, Tsutomu'
_publ_section_title
;
 Generation and amplification of optical activity of axially chiral
 N-(1-naphthyl)-2(1H)-pyrimidinethione by crystallization.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5418
_journal_page_last               5422
_journal_paper_doi               10.1039/c0ob00262c
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C16 H14 N2 S'
_chemical_formula_weight         266.35
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6223(3)
_cell_length_b                   7.6223(3)
_cell_length_c                   23.186(2)
_cell_measurement_reflns_used    2784
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.67
_cell_volume                     1347.09(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7568
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0384
_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)+(0.0512P)²+0.1383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                2583
_reflns_number_total             2928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00262c.txt
_cod_data_source_block           saka69_p43
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P4(3)
_cod_database_code               7153465
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.27765(7) 0.01243(8) 0.21078(2) 0.03903(15) Uani 1 1 d .
C8 C 0.7298(3) -0.0060(3) 0.25165(11) 0.0396(5) Uani 1 1 d .
H8 H 0.7512 -0.1066 0.2285 0.048 Uiso 1 1 calc R
C3 C 0.6440(3) 0.1513(3) 0.06956(9) 0.0331(5) Uani 1 1 d .
H3 H 0.7194 0.1811 0.0385 0.040 Uiso 1 1 calc R
C11 C 0.6730(3) 0.2937(3) 0.31822(9) 0.0348(5) Uani 1 1 d .
C2 C 0.6977(3) 0.1734(3) 0.12471(9) 0.0343(5) Uani 1 1 d .
C4 C 0.4764(3) 0.0843(3) 0.05878(9) 0.0319(5) Uani 1 1 d .
C7 C 0.6440(3) 0.1322(3) 0.22834(10) 0.0343(5) Uani 1 1 d .
C14 C 0.5099(3) 0.5841(3) 0.26992(11) 0.0392(5) Uani 1 1 d .
H14 H 0.4536 0.6844 0.2542 0.047 Uiso 1 1 calc R
C16 C 0.6143(3) 0.2857(3) 0.26025(10) 0.0344(5) Uani 1 1 d .
C15 C 0.5282(3) 0.4379(3) 0.23642(11) 0.0364(5) Uani 1 1 d .
H15 H 0.4850 0.4365 0.1980 0.044 Uiso 1 1 calc R
C1 C 0.4143(3) 0.0653(3) 0.15648(10) 0.0319(4) Uani 1 1 d .
C12 C 0.6495(3) 0.4479(4) 0.35000(11) 0.0481(6) Uani 1 1 d .
H12 H 0.6893 0.4525 0.3888 0.058 Uiso 1 1 calc R
C10 C 0.7591(3) 0.1413(4) 0.34183(11) 0.0461(6) Uani 1 1 d .
H10 H 0.7965 0.1429 0.3809 0.055 Uiso 1 1 calc R
C5 C 0.8739(3) 0.2432(3) 0.14013(11) 0.0453(6) Uani 1 1 d .
H5A H 0.9363 0.2774 0.1049 0.068 Uiso 1 1 calc R
H5B H 0.9409 0.1524 0.1604 0.068 Uiso 1 1 calc R
H5C H 0.8604 0.3458 0.1652 0.068 Uiso 1 1 calc R
C6 C 0.4162(3) 0.0472(3) -0.00135(9) 0.0411(5) Uani 1 1 d .
H6A H 0.4213 -0.0794 -0.0086 0.062 Uiso 1 1 calc R
H6B H 0.4926 0.1083 -0.0288 0.062 Uiso 1 1 calc R
H6C H 0.2953 0.0884 -0.0061 0.062 Uiso 1 1 calc R
C9 C 0.7882(3) -0.0049(3) 0.30934(11) 0.0405(6) Uani 1 1 d .
H9 H 0.8465 -0.1039 0.3252 0.049 Uiso 1 1 calc R
C13 C 0.5715(3) 0.5904(4) 0.32678(12) 0.0507(7) Uani 1 1 d .
H13 H 0.5585 0.6945 0.3489 0.061 Uiso 1 1 calc R
N1 N 0.5845(2) 0.1247(2) 0.16851(7) 0.0330(4) Uani 1 1 d .
N2 N 0.3644(2) 0.0466(2) 0.10095(8) 0.0329(4) Uani 1 1 d .
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'
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
C7 C8 C9 121.8(2)
C7 C8 H8 119.1
C9 C8 H8 119.1
C2 C3 C4 119.4(2)
C2 C3 H3 120.3
C4 C3 H3 120.3
C12 C11 C16 119.7(2)
C12 C11 C10 122.4(2)
C16 C11 C10 118.0(2)
C3 C2 N1 118.1(2)
C3 C2 C5 123.0(2)
N1 C2 C5 118.84(18)
N2 C4 C3 122.29(19)
N2 C4 C6 116.60(19)
C3 C4 C6 121.1(2)
C8 C7 C16 121.1(2)
C8 C7 N1 120.0(2)
C16 C7 N1 118.89(19)
C15 C14 C13 122.0(2)
C15 C14 H14 119.0
C13 C14 H14 119.0
C7 C16 C11 119.0(2)
C7 C16 C15 122.8(2)
C11 C16 C15 118.2(2)
C14 C15 C16 119.0(2)
C14 C15 H15 120.5
C16 C15 H15 120.5
N2 C1 N1 119.0(2)
N2 C1 S1 120.91(16)
N1 C1 S1 120.09(16)
C13 C12 C11 121.5(2)
C13 C12 H12 119.3
C11 C12 H12 119.3
C9 C10 C11 121.5(2)
C9 C10 H10 119.3
C11 C10 H10 119.3
C2 C5 H5A 109.5
C2 C5 H5B 109.5
H5A C5 H5B 109.5
C2 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C10 C9 C8 118.6(2)
C10 C9 H9 120.7
C8 C9 H9 120.7
C12 C13 C14 119.7(2)
C12 C13 H13 120.2
C14 C13 H13 120.2
C2 N1 C1 121.18(18)
C2 N1 C7 119.56(17)
C1 N1 C7 119.25(18)
C4 N2 C1 119.84(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.683(2)
C8 C7 1.352(3)
C8 C9 1.410(4)
C8 H8 0.9500
C3 C2 1.353(3)
C3 C4 1.398(3)
C3 H3 0.9500
C11 C12 1.399(3)
C11 C16 1.418(3)
C11 C10 1.442(4)
C2 N1 1.383(3)
C2 C5 1.488(3)
C4 N2 1.329(3)
C4 C6 1.495(3)
C7 C16 1.403(3)
C7 N1 1.461(3)
C14 C15 1.365(3)
C14 C13 1.400(4)
C14 H14 0.9500
C16 C15 1.443(3)
C15 H15 0.9500
C1 N2 1.350(3)
C1 N1 1.402(3)
C12 C13 1.350(4)
C12 H12 0.9500
C10 C9 1.363(4)
C10 H10 0.9500
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C9 H9 0.9500
C13 H13 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
C4 C3 C2 N1 1.4(3)
C4 C3 C2 C5 179.8(2)
C2 C3 C4 N2 2.3(3)
C2 C3 C4 C6 -176.1(2)
C9 C8 C7 C16 2.1(3)
C9 C8 C7 N1 -179.5(2)
C8 C7 C16 C11 -1.1(3)
N1 C7 C16 C11 -179.56(18)
C8 C7 C16 C15 178.0(2)
N1 C7 C16 C15 -0.5(3)
C12 C11 C16 C7 177.9(2)
C10 C11 C16 C7 -0.8(3)
C12 C11 C16 C15 -1.2(3)
C10 C11 C16 C15 -179.90(19)
C13 C14 C15 C16 -0.2(3)
C7 C16 C15 C14 -177.8(2)
C11 C16 C15 C14 1.3(3)
C16 C11 C12 C13 0.1(3)
C10 C11 C12 C13 178.7(2)
C12 C11 C10 C9 -176.9(2)
C16 C11 C10 C9 1.8(3)
C11 C10 C9 C8 -0.9(3)
C7 C8 C9 C10 -1.1(4)
C11 C12 C13 C14 1.0(4)
C15 C14 C13 C12 -1.0(4)
C3 C2 N1 C1 -4.3(3)
C5 C2 N1 C1 177.2(2)
C3 C2 N1 C7 174.6(2)
C5 C2 N1 C7 -3.9(3)
N2 C1 N1 C2 3.7(3)
S1 C1 N1 C2 -178.23(17)
N2 C1 N1 C7 -175.25(19)
S1 C1 N1 C7 2.9(3)
C8 C7 N1 C2 -86.6(3)
C16 C7 N1 C2 91.9(2)
C8 C7 N1 C1 92.4(2)
C16 C7 N1 C1 -89.1(2)
C3 C4 N2 C1 -3.1(3)
C6 C4 N2 C1 175.44(19)
N1 C1 N2 C4 0.1(3)
S1 C1 N2 C4 -178.02(15)
