#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:59:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180117 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/15/7101531.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_7101531
loop_
_publ_author_name
'Suad Rashdan'
'Mark E. Light'
'Jeremy D. Kilburn'
_publ_section_title
;
Pyridyl thioureas as switchable anion receptors
;
_journal_issue                   44
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b611138f
_journal_year                    2006
_chemical_compound_source        'Suad Rashdan'
_chemical_formula_sum            'C12 H14 B F4 N3 O S'
_chemical_formula_weight         335.13
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.363(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2690(6)
_cell_length_b                   22.1000(15)
_cell_length_c                   7.1372(3)
_cell_measurement_reflns_used    3235
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1449.96(15)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18054
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0537
_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)+(0.0560P)²+1.1188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                2160
_reflns_number_total             3311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b611138f.txt
_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 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7101531
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_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 0.2452(2) 0.33238(10) -0.0837(4) 0.0317(5) Uani 1 1 d .
H99 H 0.262(4) 0.3205(17) 0.027(6) 0.061(13) Uiso 1 1 d .
H98 H 0.242(4) 0.301(2) -0.154(6) 0.074(14) Uiso 1 1 d .
C1 C -0.2339(3) 0.39166(13) 0.2903(4) 0.0296(6) Uani 1 1 d .
H1 H -0.1856 0.3548 0.3092 0.036 Uiso 1 1 calc R
C2 C -0.3803(3) 0.39399(13) 0.2882(4) 0.0326(7) Uani 1 1 d .
H2 H -0.4331 0.3590 0.3042 0.039 Uiso 1 1 calc R
C3 C -0.4499(3) 0.44956(13) 0.2618(4) 0.0330(7) Uani 1 1 d .
H3 H -0.5502 0.4518 0.2606 0.040 Uiso 1 1 calc R
C4 C -0.3722(3) 0.50111(13) 0.2375(4) 0.0311(6) Uani 1 1 d .
H4 H -0.4192 0.5382 0.2201 0.037 Uiso 1 1 calc R
C5 C -0.2209(3) 0.49719(12) 0.2393(4) 0.0256(6) Uani 1 1 d .
C6 C 0.0058(3) 0.55726(12) 0.2106(4) 0.0246(6) Uani 1 1 d .
C7 C 0.1609(3) 0.64632(12) 0.1454(4) 0.0252(6) Uani 1 1 d .
C8 C 0.1417(3) 0.70170(13) 0.0501(4) 0.0273(6) Uani 1 1 d .
H8 H 0.0486 0.7149 0.0041 0.033 Uiso 1 1 calc R
C9 C 0.2610(3) 0.73653(13) 0.0246(4) 0.0292(6) Uani 1 1 d .
H9 H 0.2483 0.7728 -0.0414 0.035 Uiso 1 1 calc R
C10 C 0.3995(3) 0.71782(13) 0.0967(4) 0.0305(6) Uani 1 1 d .
H10 H 0.4797 0.7415 0.0794 0.037 Uiso 1 1 calc R
C11 C 0.4182(3) 0.66408(13) 0.1942(4) 0.0295(6) Uani 1 1 d .
H11 H 0.5113 0.6519 0.2440 0.035 Uiso 1 1 calc R
C12 C 0.2996(3) 0.62773(13) 0.2190(4) 0.0271(6) Uani 1 1 d .
H12 H 0.3131 0.5913 0.2843 0.033 Uiso 1 1 calc R
N1 N -0.1573(2) 0.44286(10) 0.2649(3) 0.0258(5) Uani 1 1 d .
H1A H -0.0647 0.4403 0.2653 0.031 Uiso 1 1 calc R
N2 N -0.1424(2) 0.54845(10) 0.2143(3) 0.0283(5) Uani 1 1 d .
H2A H -0.1938 0.5809 0.1980 0.034 Uiso 1 1 calc R
N3 N 0.0304(2) 0.61463(10) 0.1648(3) 0.0282(5) Uani 1 1 d .
H3A H -0.0470 0.6363 0.1432 0.034 Uiso 1 1 calc R
S1 S 0.12878(7) 0.50242(3) 0.25789(10) 0.0293(2) Uani 1 1 d .
B1 B 0.2061(3) 0.33593(15) 0.4079(5) 0.0305(7) Uani 1 1 d .
F1 F 0.29302(19) 0.30227(8) 0.3002(2) 0.0467(5) Uani 1 1 d .
F2 F 0.1607(2) 0.29848(9) 0.5444(3) 0.0585(6) Uani 1 1 d .
F3 F 0.08646(18) 0.35694(8) 0.2904(3) 0.0442(5) Uani 1 1 d .
F4 F 0.28656(17) 0.38353(8) 0.4935(2) 0.0387(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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
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
C2 C1 N1 120.4(3)
C1 C2 C3 118.8(3)
C4 C3 C2 120.6(3)
C3 C4 C5 119.2(3)
N1 C5 N2 121.8(2)
N1 C5 C4 118.5(2)
N2 C5 C4 119.6(2)
N3 C6 N2 109.7(2)
N3 C6 S1 127.3(2)
N2 C6 S1 123.0(2)
C12 C7 C8 119.8(2)
C12 C7 N3 125.2(2)
C8 C7 N3 114.9(2)
C9 C8 C7 119.9(2)
C8 C9 C10 120.4(3)
C11 C10 C9 119.8(3)
C10 C11 C12 120.8(3)
C7 C12 C11 119.3(3)
C5 N1 C1 122.4(2)
C5 N2 C6 131.3(2)
C6 N3 C7 131.8(2)
F3 B1 F2 109.6(2)
F3 B1 F4 110.9(3)
F2 B1 F4 109.8(2)
F3 B1 F1 108.7(2)
F2 B1 F1 108.5(3)
F4 B1 F1 109.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.356(4)
C1 N1 1.360(3)
C2 C3 1.389(4)
C3 C4 1.371(4)
C4 C5 1.404(4)
C5 N1 1.339(3)
C5 N2 1.370(3)
C6 N3 1.336(3)
C6 N2 1.391(3)
C6 S1 1.668(3)
C7 C12 1.387(4)
C7 C8 1.400(4)
C7 N3 1.420(3)
C8 C9 1.379(4)
C9 C10 1.383(4)
C10 C11 1.376(4)
C11 C12 1.392(4)
B1 F3 1.382(4)
B1 F2 1.384(4)
B1 F4 1.385(4)
B1 F1 1.397(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H99 F1 0.83(4) 1.98(4) 2.800(3) 173(4) .
O1 H98 F2 0.85(5) 2.19(4) 2.772(3) 126(4) 1_554
O1 H98 F1 0.85(5) 2.37(5) 3.135(3) 150(4) 4_565
N1 H1A S1 0.86 2.27 2.967(2) 138.8 .
N1 H1A F3 0.86 2.31 2.939(3) 130.5 .
N3 H3A O1 0.86 1.96 2.803(3) 166.8 3_565
N2 H2A F4 0.86 2.59 3.018(3) 112.2 3_566
