#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:51:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180452 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/21/7212185.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_7212185
loop_
_publ_author_name
'Kinuta, Takafumi'
'Yokoyama, Emi'
'Sato, Tomohiro'
'Tajima, Nobuo'
'Kuroda, Reiko'
'Matsubara, Yoshio'
'Imai, Yoshitane'
_publ_section_title
;
 Development of novel thioether compound for spontaneous chiral
 crystallization
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              1394
_journal_paper_doi               10.1039/b921416j
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C20 H13 N O2 S'
_chemical_formula_weight         331.37
_chemical_name_systematic
;
?
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.3860(10)
_cell_angle_beta                 98.5840(10)
_cell_angle_gamma                105.8040(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7637(6)
_cell_length_b                   8.5895(6)
_cell_length_c                   12.7850(9)
_cell_measurement_reflns_used    3075
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      1.70
_cell_volume                     768.08(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω 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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6801
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9674
_exptl_absorpt_correction_T_min  0.9065
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.3489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                3075
_reflns_number_total             3434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b921416j.txt
_cod_data_source_block           imai913_3
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        768.07(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7212185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.50981(15) -0.02034(15) 0.69926(9) 0.0256(3) Uani 1 1 d .
O4 O 0.22636(18) 0.28912(15) 0.45042(10) 0.0342(3) Uani 1 1 d .
C1 C 0.4110(2) 0.03858(19) 0.65047(12) 0.0201(3) Uani 1 1 d .
C2 C 0.41362(19) 0.21860(19) 0.69818(12) 0.0200(3) Uani 1 1 d .
C3 C 0.3613(2) 0.30381(19) 0.63145(13) 0.0226(3) Uani 1 1 d .
C4 C 0.2670(2) 0.2103(2) 0.51109(13) 0.0230(3) Uani 1 1 d .
C5 C 0.1050(2) -0.0734(2) 0.36427(13) 0.0247(3) Uani 1 1 d .
H5 H 0.0564 -0.0179 0.3179 0.030 Uiso 1 1 calc R
C6 C 0.0638(2) -0.2488(2) 0.32673(13) 0.0289(4) Uani 1 1 d .
H6 H -0.0145 -0.3138 0.2548 0.035 Uiso 1 1 calc R
C7 C 0.1366(2) -0.3306(2) 0.39363(14) 0.0306(4) Uani 1 1 d .
H7 H 0.1085 -0.4511 0.3671 0.037 Uiso 1 1 calc R
C8 C 0.2496(2) -0.2369(2) 0.49855(13) 0.0266(3) Uani 1 1 d .
H8 H 0.3002 -0.2929 0.5438 0.032 Uiso 1 1 calc R
C9 C 0.2892(2) -0.06087(19) 0.53792(12) 0.0205(3) Uani 1 1 d .
C10 C 0.2177(2) 0.02160(19) 0.47016(12) 0.0206(3) Uani 1 1 d .
C11 C 0.3878(3) 0.4911(2) 0.66911(14) 0.0335(4) Uani 1 1 d .
H11A H 0.4279 0.5368 0.7508 0.050 Uiso 1 1 calc R
H11B H 0.2711 0.5091 0.6446 0.050 Uiso 1 1 calc R
H11C H 0.4816 0.5500 0.6366 0.050 Uiso 1 1 calc R
S12 S 0.51593(5) 0.32299(5) 0.84132(3) 0.02368(13) Uani 1 1 d .
N13 N 0.25145(16) 0.04622(15) 0.83822(10) 0.0177(3) Uani 1 1 d .
C14 C 0.39394(19) 0.17697(18) 0.90144(12) 0.0175(3) Uani 1 1 d .
C15 C 0.4605(2) 0.21642(18) 1.01795(12) 0.0193(3) Uani 1 1 d .
H15 H 0.5648 0.3140 1.0589 0.023 Uiso 1 1 calc R
C16 C 0.3713(2) 0.11104(18) 1.06948(12) 0.0192(3) Uani 1 1 d .
H16 H 0.4101 0.1358 1.1479 0.023 Uiso 1 1 calc R
C17 C 0.1245(2) -0.15609(19) 1.05176(13) 0.0214(3) Uani 1 1 d .
H17 H 0.1592 -0.1376 1.1297 0.026 Uiso 1 1 calc R
C18 C -0.0177(2) -0.29868(19) 0.98461(14) 0.0237(3) Uani 1 1 d .
H18 H -0.0811 -0.3791 1.0161 0.028 Uiso 1 1 calc R
C19 C -0.0702(2) -0.32634(19) 0.86942(13) 0.0243(3) Uani 1 1 d .
H19 H -0.1687 -0.4259 0.8238 0.029 Uiso 1 1 calc R
C20 C 0.0181(2) -0.21247(18) 0.82188(12) 0.0207(3) Uani 1 1 d .
H20 H -0.0193 -0.2329 0.7439 0.025 Uiso 1 1 calc R
C21 C 0.16512(19) -0.06455(17) 0.88907(12) 0.0170(3) Uani 1 1 d .
C22 C 0.21948(19) -0.03656(18) 1.00510(12) 0.0174(3) 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'
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
O1 C1 C9 121.61(14)
O1 C1 C2 121.64(14)
C9 C1 C2 116.67(13)
C3 C2 C1 121.04(14)
C3 C2 S12 121.17(12)
C1 C2 S12 117.26(11)
C2 C3 C4 120.06(14)
C2 C3 C11 124.60(14)
C4 C3 C11 115.34(13)
O4 C4 C10 121.67(14)
O4 C4 C3 119.66(14)
C10 C4 C3 118.60(13)
C6 C5 C10 119.83(15)
C5 C6 C7 120.37(15)
C8 C7 C6 120.11(15)
C7 C8 C9 120.00(15)
C8 C9 C10 119.87(14)
C8 C9 C1 119.61(14)
C10 C9 C1 120.50(14)
C5 C10 C9 119.81(14)
C5 C10 C4 120.70(14)
C9 C10 C4 119.47(13)
C2 S12 C14 101.59(7)
C14 N13 C21 116.73(12)
N13 C14 C15 125.29(13)
N13 C14 S12 119.43(11)
C15 C14 S12 115.27(10)
C16 C15 C14 118.21(13)
C15 C16 C22 119.40(13)
C18 C17 C22 120.00(14)
C17 C18 C19 120.25(13)
C20 C19 C18 121.15(14)
C19 C20 C21 119.79(14)
N13 C21 C20 118.13(13)
N13 C21 C22 122.54(13)
C20 C21 C22 119.32(13)
C17 C22 C21 119.48(13)
C17 C22 C16 122.77(13)
C21 C22 C16 117.74(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2123(18)
O4 C4 1.2172(19)
C1 C9 1.482(2)
C1 C2 1.497(2)
C2 C3 1.348(2)
C2 S12 1.7582(15)
C3 C4 1.496(2)
C3 C11 1.497(2)
C4 C10 1.483(2)
C5 C6 1.382(2)
C5 C10 1.391(2)
C6 C7 1.391(2)
C7 C8 1.381(2)
C8 C9 1.390(2)
C9 C10 1.399(2)
S12 C14 1.7728(14)
N13 C14 1.3088(18)
N13 C21 1.3741(17)
C14 C15 1.417(2)
C15 C16 1.358(2)
C16 C22 1.420(2)
C17 C18 1.371(2)
C17 C22 1.4135(19)
C18 C19 1.405(2)
C19 C20 1.368(2)
C20 C21 1.4117(19)
C21 C22 1.416(2)
