#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:32:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178472 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/93/4029302.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_4029302
loop_
_publ_author_name
'Hua, Guoxiong'
'Du, Junyi'
'Slawin, Alexandra M. Z.'
'Woollins, J. Derek'
_publ_section_title
;
 2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF5 Groups: A
 Synthetic and Structural Study.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3876
_journal_page_last               3886
_journal_paper_doi               10.1021/jo500316v
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C15 H9 Cl F5 N S Se'
_chemical_formula_sum            'C15 H9 Cl F5 N S Se'
_chemical_formula_weight         444.71
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.536(3)
_cell_length_b                   6.7909(12)
_cell_length_c                   18.646(4)
_cell_measurement_reflns_used    12307
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.00
_cell_volume                     1587.3(6)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r12'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r12'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1126
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15600
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.715
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chip
_exptl_crystal_F_000             872.00
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0326P)²+1.5183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                1467
_reflns_number_total             1972
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo500316v_si_001.cif
_cod_data_source_block           User-defined
_cod_depositor_comments
'Adding full bibliography for 4029302--4029308.cif.'
_cod_original_cell_volume        1587.3(5)
_cod_database_code               4029302
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2+Z
3 +X,1/2-Y,+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,1/2-Z
7 -X,1/2+Y,-Z
8 1/2+X,+Y,1/2-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
Se3 Se 0.56501(5) 0.2500 1.12421(3) 0.0410(3) Uani 1.0 4 d .
Cl1 Cl 0.78517(14) 0.2500 0.68748(9) 0.0603(6) Uani 1.0 4 d .
S1 S -0.01247(12) 0.2500 1.13456(8) 0.0385(4) Uani 1.0 4 d .
F1 F 0.00332(18) 0.4122(4) 1.19381(14) 0.0555(8) Uani 1.0 8 d .
F2 F -0.0393(2) 0.4146(6) 1.07806(17) 0.0912(13) Uani 1.0 8 d .
F3 F -0.1357(3) 0.2500 1.1555(2) 0.0636(12) Uani 1.0 4 d .
N1 N 0.4885(3) 0.2500 0.9892(2) 0.0237(10) Uani 1.0 4 d .
C2 C 0.4550(4) 0.2500 1.0549(3) 0.0253(12) Uani 1.0 4 d .
C4 C 0.6535(4) 0.2500 1.0457(3) 0.0372(15) Uani 1.0 4 d .
C5 C 0.5988(4) 0.2500 0.9836(3) 0.0242(12) Uani 1.0 4 d .
C6 C 0.3421(4) 0.2500 1.0758(3) 0.0218(11) Uani 1.0 4 d .
C7 C 0.2641(4) 0.2500 1.0222(3) 0.0298(13) Uani 1.0 4 d .
C8 C 0.1572(4) 0.2500 1.0397(3) 0.0280(13) Uani 1.0 4 d .
C9 C 0.1274(4) 0.2500 1.1110(3) 0.0260(13) Uani 1.0 4 d .
C10 C 0.2028(4) 0.2500 1.1651(3) 0.0277(13) Uani 1.0 4 d .
C11 C 0.3087(4) 0.2500 1.1472(3) 0.0258(12) Uani 1.0 4 d .
C12 C 0.6461(4) 0.2500 0.9111(3) 0.0240(12) Uani 1.0 4 d .
C13 C 0.5805(4) 0.2500 0.8506(3) 0.0282(13) Uani 1.0 4 d .
C14 C 0.6225(4) 0.2500 0.7827(3) 0.0312(14) Uani 1.0 4 d .
C15 C 0.7314(4) 0.2500 0.7739(3) 0.0332(14) Uani 1.0 4 d .
C16 C 0.7991(4) 0.2500 0.8323(3) 0.0323(14) Uani 1.0 4 d .
C17 C 0.7566(4) 0.2500 0.9004(3) 0.0301(13) Uani 1.0 4 d .
H4 H 0.7291 0.2500 1.0487 0.0446 Uiso 1.0 4 calc R
H7 H 0.2849 0.2500 0.9733 0.0357 Uiso 1.0 4 calc R
H8 H 0.1046 0.2500 1.0031 0.0336 Uiso 1.0 4 calc R
H10 H 0.1814 0.2500 1.2139 0.0332 Uiso 1.0 4 calc R
H11 H 0.3607 0.2500 1.1843 0.0309 Uiso 1.0 4 calc R
H13 H 0.5052 0.2500 0.8565 0.0339 Uiso 1.0 4 calc R
H14 H 0.5768 0.2500 0.7420 0.0374 Uiso 1.0 4 calc R
H16 H 0.8742 0.2500 0.8256 0.0388 Uiso 1.0 4 calc R
H17 H 0.8029 0.2500 0.9407 0.0361 Uiso 1.0 4 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 Se3 C4 84.0(3) yes . .
F1 S1 F1 88.94(16) yes . 3_555
F1 S1 F2 89.97(17) yes . .
F1 S1 F2 174.59(17) yes . 3_555
F1 S1 F3 87.13(15) yes . .
F1 S1 C9 92.79(17) yes . .
F1 S1 F2 174.59(17) yes 3_555 .
F1 S1 F2 89.97(17) yes 3_555 3_555
F1 S1 F3 87.13(15) yes 3_555 .
F1 S1 C9 92.79(17) yes 3_555 .
F2 S1 F2 90.6(2) yes . 3_555
F2 S1 F3 87.53(15) yes . .
F2 S1 C9 92.56(17) yes . .
F2 S1 F3 87.53(15) yes 3_555 .
F2 S1 C9 92.56(17) yes 3_555 .
F3 S1 C9 179.9(3) yes . .
C2 N1 C5 113.2(5) yes . .
Se3 C2 N1 114.2(4) yes . .
Se3 C2 C6 121.5(4) yes . .
N1 C2 C6 124.3(5) yes . .
Se3 C4 C5 112.2(4) yes . .
N1 C5 C4 116.3(5) yes . .
N1 C5 C12 118.0(5) yes . .
C4 C5 C12 125.7(5) yes . .
C2 C6 C7 119.0(5) yes . .
C2 C6 C11 122.9(5) yes . .
C7 C6 C11 118.2(5) yes . .
C6 C7 C8 120.7(5) yes . .
C7 C8 C9 119.4(5) yes . .
S1 C9 C8 119.8(4) yes . .
S1 C9 C10 119.1(5) yes . .
C8 C9 C10 121.2(5) yes . .
C9 C10 C11 119.0(6) yes . .
C6 C11 C10 121.6(5) yes . .
C5 C12 C13 120.2(5) yes . .
C5 C12 C17 121.9(5) yes . .
C13 C12 C17 117.9(5) yes . .
C12 C13 C14 121.3(5) yes . .
C13 C14 C15 119.4(5) yes . .
Cl1 C15 C14 119.6(5) yes . .
Cl1 C15 C16 119.4(4) yes . .
C14 C15 C16 121.1(5) yes . .
C15 C16 C17 119.3(5) yes . .
C12 C17 C16 121.0(5) yes . .
Se3 C4 H4 123.835 no . .
C5 C4 H4 123.954 no . .
C6 C7 H7 119.650 no . .
C8 C7 H7 119.661 no . .
C7 C8 H8 120.334 no . .
C9 C8 H8 120.286 no . .
C9 C10 H10 120.426 no . .
C11 C10 H10 120.548 no . .
C6 C11 H11 119.262 no . .
C10 C11 H11 119.167 no . .
C12 C13 H13 119.398 no . .
C14 C13 H13 119.275 no . .
C13 C14 H14 120.324 no . .
C15 C14 H14 120.242 no . .
C15 C16 H16 120.339 no . .
C17 C16 H16 120.355 no . .
C12 C17 H17 119.532 no . .
C16 C17 H17 119.510 no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
Se3 C2 1.890(6) yes .
Se3 C4 1.837(6) yes .
Cl1 C15 1.747(6) yes .
S1 F1 1.573(3) yes .
S1 F1 1.573(3) yes 3_555
S1 F2 1.572(4) yes .
S1 F2 1.572(4) yes 3_555
S1 F3 1.593(4) yes .
S1 C9 1.808(6) yes .
N1 C2 1.295(7) yes .
N1 C5 1.387(7) yes .
C2 C6 1.468(8) yes .
C4 C5 1.346(8) yes .
C5 C12 1.476(8) yes .
C6 C7 1.398(8) yes .
C6 C11 1.396(8) yes .
C7 C8 1.379(8) yes .
C8 C9 1.381(8) yes .
C9 C10 1.382(8) yes .
C10 C11 1.369(8) yes .
C12 C13 1.396(8) yes .
C12 C17 1.399(8) yes .
C13 C14 1.371(8) yes .
C14 C15 1.375(7) yes .
C15 C16 1.381(8) yes .
C16 C17 1.377(8) yes .
C4 H4 0.950 no .
C7 H7 0.949 no .
C8 H8 0.949 no .
C10 H10 0.949 no .
C11 H11 0.950 no .
C13 H13 0.950 no .
C14 H14 0.950 no .
C16 H16 0.950 no .
C17 H17 0.949 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_2
Se3 C11 3.242(5) no .
F1 C10 2.785(6) no .
F2 C8 2.798(6) no .
N1 C7 2.880(7) no .
N1 C13 2.830(7) no .
C2 C12 3.596(8) no .
C4 C17 3.002(8) no .
C6 C9 2.770(8) no .
C7 C10 2.773(8) no .
C8 C11 2.761(8) no .
C12 C15 2.773(8) no .
C13 C16 2.761(8) no .
C14 C17 2.764(8) no .
F1 C14 3.240(5) no 2_555
F1 C16 3.411(5) no 5_667
F2 F2 3.285(5) no 5_567
F2 C8 3.492(6) no 5_567
F3 C4 3.343(7) no 1_455
N1 N1 3.4314(10) no 5_657
N1 N1 3.4314(10) no 5_667
N1 C2 3.565(2) no 5_657
N1 C2 3.565(2) no 5_667
C2 N1 3.565(2) no 5_657
C2 N1 3.565(2) no 5_667
C2 C5 3.535(3) no 5_657
C2 C5 3.535(3) no 5_667
C4 F3 3.343(7) no 1_655
C5 C2 3.535(3) no 5_657
C5 C2 3.535(3) no 5_667
C6 C12 3.4074(9) no 5_657
C6 C12 3.4074(9) no 5_667
C8 F2 3.492(6) no 5_567
C8 F2 3.492(6) no 7_547
C10 C16 3.3959(6) no 5_657
C10 C16 3.3959(6) no 5_667
C12 C6 3.4074(9) no 5_657
C12 C6 3.4074(9) no 5_667
C14 F1 3.240(5) no 2_544
C14 F1 3.240(5) no 4_564
C16 F1 3.411(5) no 5_667
C16 F1 3.411(5) no 7_647
C16 C10 3.3959(6) no 5_657
C16 C10 3.3959(6) no 5_667
Se3 H11 2.7960 no .
Cl1 H14 2.8035 no .
Cl1 H16 2.8062 no .
S1 H8 2.8569 no .
S1 H10 2.8452 no .
F1 H10 2.5172 no .
F2 H8 2.5410 no .
N1 H4 3.2139 no .
N1 H7 2.5690 no .
N1 H13 2.4824 no .
C2 H4 3.4387 no .
C2 H7 2.6195 no .
C2 H11 2.6869 no .
C4 H17 2.7101 no .
C5 H13 2.6436 no .
C5 H17 2.6813 no .
C6 H8 3.2716 no .
C6 H10 3.2702 no .
C7 H11 3.2556 no .
C8 H10 3.2629 no .
C9 H7 3.2398 no .
C9 H11 3.2275 no .
C10 H8 3.2621 no .
C11 H7 3.2569 no .
C12 H4 2.7680 no .
C12 H14 3.2696 no .
C12 H16 3.2740 no .
C13 H17 3.2551 no .
C14 H16 3.2548 no .
C15 H13 3.2270 no .
C15 H17 3.2363 no .
C16 H14 3.2556 no .
C17 H4 2.7855 no .
C17 H13 3.2556 no .
H4 H17 2.2157 no .
H7 H8 2.3284 no .
H7 H13 3.5159 no .
H10 H11 2.3144 no .
H13 H14 2.3156 no .
H16 H17 2.3246 no .
Se3 H10 3.3518 no 6_557
Se3 H13 3.5260 no 5_657
Se3 H13 3.5260 no 5_667
Cl1 H7 2.9971 no 6_556
Cl1 H13 2.8780 no 6_556
F1 H11 3.0949 no 6_457
F1 H14 2.6606 no 2_555
F1 H16 2.7838 no 5_667
F2 H4 3.1586 no 1_455
F2 H8 2.8541 no 5_567
F2 H16 3.5636 no 5_667
F2 H17 3.4240 no 1_455
F3 H4 2.6153 no 1_455
F3 H10 3.3444 no 6_457
F3 H11 2.9876 no 6_457
C4 H7 3.4999 no 5_657
C4 H7 3.4999 no 5_667
C7 H17 3.5658 no 5_657
C7 H17 3.5658 no 5_667
C8 H17 3.4515 no 5_657
C8 H17 3.4515 no 5_667
C9 H16 3.5956 no 5_657
C9 H16 3.5956 no 5_667
C10 H16 3.5342 no 5_657
C10 H16 3.5342 no 5_667
C13 H11 3.5350 no 5_657
C13 H11 3.5350 no 5_667
C14 H11 3.4572 no 5_657
C14 H11 3.4572 no 5_667
C15 H10 3.5744 no 5_657
C15 H10 3.5744 no 5_667
C16 H10 3.5117 no 5_657
C16 H10 3.5117 no 5_667
H4 F2 3.1586 no 1_655
H4 F2 3.1586 no 3_655
H4 F3 2.6153 no 1_655
H4 H7 3.4245 no 5_657
H4 H7 3.4245 no 5_667
H7 Cl1 2.9971 no 6_456
H7 C4 3.4999 no 5_657
H7 C4 3.4999 no 5_667
H7 H4 3.4245 no 5_657
H7 H4 3.4245 no 5_667
H8 F2 2.8541 no 5_567
H8 F2 2.8541 no 7_547
H10 Se3 3.3518 no 6_457
H10 F3 3.3444 no 6_557
H10 C15 3.5744 no 5_657
H10 C15 3.5744 no 5_667
H10 C16 3.5117 no 5_657
H10 C16 3.5117 no 5_667
H10 H16 3.5436 no 5_657
H10 H16 3.5436 no 5_667
H11 F1 3.0949 no 6_557
H11 F1 3.0949 no 8_557
H11 F3 2.9876 no 6_557
H11 C13 3.5350 no 5_657
H11 C13 3.5350 no 5_667
H11 C14 3.4572 no 5_657
H11 C14 3.4572 no 5_667
H13 Se3 3.5260 no 5_657
H13 Se3 3.5260 no 5_667
H13 Cl1 2.8780 no 6_456
H14 F1 2.6606 no 2_544
H14 F1 2.6606 no 4_564
H14 H16 2.8354 no 6_456
H16 F1 2.7838 no 5_667
H16 F1 2.7838 no 7_647
H16 F2 3.5636 no 5_667
H16 F2 3.5636 no 7_647
H16 C9 3.5956 no 5_657
H16 C9 3.5956 no 5_667
H16 C10 3.5342 no 5_657
H16 C10 3.5342 no 5_667
H16 H10 3.5436 no 5_657
H16 H10 3.5436 no 5_667
H16 H14 2.8354 no 6_556
H17 F2 3.4240 no 1_655
H17 F2 3.4240 no 3_655
H17 C7 3.5658 no 5_657
H17 C7 3.5658 no 5_667
H17 C8 3.4515 no 5_657
H17 C8 3.4515 no 5_667
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
_geom_torsion_site_symmetry_1
C2 Se3 C4 C5 0.0 no .
C4 Se3 C2 N1 0.0 no .
C4 Se3 C2 C6 180.0 no .
F1 S1 C9 C8 -135.47(11) no .
F1 S1 C9 C10 44.53(11) no .
F1 S1 C9 C8 135.47(11) no 3_555
F1 S1 C9 C10 -44.53(11) no 3_555
F2 S1 C9 C8 -45.37(14) no .
F2 S1 C9 C10 134.63(14) no .
F2 S1 C9 C8 45.37(14) no 3_555
F2 S1 C9 C10 -134.63(14) no 3_555
C2 N1 C5 C4 0.0 no .
C2 N1 C5 C12 180.0 no .
C5 N1 C2 Se3 0.0 no .
C5 N1 C2 C6 180.0 no .
Se3 C2 C6 C7 180.0 no .
Se3 C2 C6 C11 0.0 no .
N1 C2 C6 C7 0.0 no .
N1 C2 C6 C11 180.0 no .
Se3 C4 C5 N1 0.0 no .
Se3 C4 C5 C12 180.0 no .
N1 C5 C12 C13 0.0 no .
N1 C5 C12 C17 180.0 no .
C4 C5 C12 C13 180.0 no .
C4 C5 C12 C17 0.0 no .
C2 C6 C7 C8 180.0 no .
C2 C6 C11 C10 180.0 no .
C7 C6 C11 C10 0.0 no .
C11 C6 C7 C8 0.0 no .
C6 C7 C8 C9 0.0 no .
C7 C8 C9 S1 180.0 no .
C7 C8 C9 C10 0.0 no .
S1 C9 C10 C11 180.0 no .
C8 C9 C10 C11 0.0 no .
C9 C10 C11 C6 0.0 no .
C5 C12 C13 C14 180.0 no .
C5 C12 C17 C16 180.0 no .
C13 C12 C17 C16 0.0 no .
C17 C12 C13 C14 0.0 no .
C12 C13 C14 C15 0.0 no .
C13 C14 C15 Cl1 180.0 no .
C13 C14 C15 C16 0.0 no .
Cl1 C15 C16 C17 180.0 no .
C14 C15 C16 C17 0.0 no .
C15 C16 C17 C12 0.0 no .
