#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:29:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178784 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/38/4103833.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_4103833
loop_
_publ_author_name
'Vivian Wing-Wah Yam'
'Jason Ka-Wai Lee'
'Chi-Chiu Ko'
'Nianyong Zhu'
_publ_section_title
;
 Photochromic Diarylethene-Containing Ionic Liquids and N-Heterocyclic
 Carbenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              912
_journal_page_last               913
_journal_paper_doi               10.1021/ja808791e
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C17 H21 F6 N2 P S2'
_chemical_formula_sum            'C17 H21 F6 N2 P S2'
_chemical_formula_weight         462.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.54(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0060(18)
_cell_length_b                   20.473(4)
_cell_length_c                   11.705(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2033.9(8)
_computing_cell_refinement       scalepack
_computing_data_collection       marcontrol
_computing_data_reduction        denzo
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'marresearch IPDS mar300'
_diffrn_measurement_method       oacillation
_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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11233
_diffrn_reflns_theta_full        25.55
_diffrn_reflns_theta_max         25.55
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    ride-on
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0397
_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)+(0.0560P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                2303
_reflns_number_total             3484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808791e_si_003.cif
_cod_data_source_block           L2
_cod_original_cell_volume        2033.9(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4103833
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.11350(8) 0.07805(3) 0.04834(6) 0.0516(2) Uani 1 1 d .
S2 S -0.44403(9) -0.03591(3) -0.33553(7) 0.0611(2) Uani 1 1 d .
N1 N -0.1450(3) 0.23274(8) -0.28639(18) 0.0461(5) Uani 1 1 d .
N2 N -0.3831(2) 0.20067(9) -0.38247(18) 0.0472(5) Uani 1 1 d .
C1 C 0.3938(3) 0.08509(13) -0.0069(3) 0.0652(8) Uani 1 1 d .
H1A H 0.4277 0.0627 0.0695 0.098 Uiso 0.50 1 calc PR
H1B H 0.4519 0.1250 0.0001 0.098 Uiso 0.50 1 calc PR
H1C H 0.4120 0.0579 -0.0677 0.098 Uiso 0.50 1 calc PR
H1D H 0.4334 0.1011 -0.0682 0.098 Uiso 0.50 1 calc PR
H1E H 0.4091 0.0387 0.0011 0.098 Uiso 0.50 1 calc PR
H1F H 0.4491 0.1058 0.0690 0.098 Uiso 0.50 1 calc PR
C2 C 0.2210(3) 0.10022(11) -0.0424(2) 0.0465(6) Uani 1 1 d .
C3 C 0.1270(3) 0.13110(10) -0.1432(2) 0.0475(6) Uani 1 1 d .
H3 H 0.1630 0.1463 -0.2041 0.057 Uiso 1 1 calc R
C4 C -0.0322(3) 0.13802(9) -0.1470(2) 0.0393(6) Uani 1 1 d .
C5 C -0.0580(3) 0.11148(10) -0.0479(2) 0.0416(6) Uani 1 1 d .
C6 C -0.2041(3) 0.10910(13) -0.0147(2) 0.0573(7) Uani 1 1 d .
H6A H -0.1827 0.0865 0.0610 0.086 Uiso 0.50 1 calc PR
H6B H -0.2852 0.0864 -0.0768 0.086 Uiso 0.50 1 calc PR
H6C H -0.2384 0.1528 -0.0070 0.086 Uiso 0.50 1 calc PR
H6D H -0.2882 0.1306 -0.0762 0.086 Uiso 0.50 1 calc PR
H6E H -0.1856 0.1307 0.0616 0.086 Uiso 0.50 1 calc PR
H6F H -0.2325 0.0644 -0.0082 0.086 Uiso 0.50 1 calc PR
C7 C -0.7382(4) -0.01311(15) -0.3066(3) 0.0850(10) Uani 1 1 d .
H7A H -0.7400 -0.0596 -0.3171 0.128 Uiso 0.50 1 calc PR
H7B H -0.8252 0.0061 -0.3692 0.128 Uiso 0.50 1 calc PR
H7C H -0.7464 -0.0029 -0.2288 0.128 Uiso 0.50 1 calc PR
H7D H -0.8010 0.0220 -0.2930 0.128 Uiso 0.50 1 calc PR
H7E H -0.7158 -0.0437 -0.2408 0.128 Uiso 0.50 1 calc PR
H7F H -0.7947 -0.0347 -0.3812 0.128 Uiso 0.50 1 calc PR
C8 C -0.5857(3) 0.01387(12) -0.3137(2) 0.0565(7) Uani 1 1 d .
C9 C -0.5360(3) 0.07653(11) -0.3029(2) 0.0514(7) Uani 1 1 d .
H9 H -0.5957 0.1110 -0.2897 0.062 Uiso 1 1 calc R
C10 C -0.3840(3) 0.08527(10) -0.3133(2) 0.0414(6) Uani 1 1 d .
C11 C -0.3176(3) 0.02791(11) -0.3307(2) 0.0462(6) Uani 1 1 d .
C12 C -0.1625(3) 0.01570(12) -0.3477(3) 0.0651(8) Uani 1 1 d .
H12A H -0.1498 -0.0303 -0.3574 0.098 Uiso 0.50 1 calc PR
H12B H -0.0789 0.0311 -0.2780 0.098 Uiso 0.50 1 calc PR
H12C H -0.1593 0.0384 -0.4186 0.098 Uiso 0.50 1 calc PR
H12D H -0.1089 0.0565 -0.3452 0.098 Uiso 0.50 1 calc PR
H12E H -0.1797 -0.0050 -0.4247 0.098 Uiso 0.50 1 calc PR
H12F H -0.0994 -0.0122 -0.2841 0.098 Uiso 0.50 1 calc PR
C13 C -0.1576(3) 0.16937(10) -0.2459(2) 0.0395(6) Uani 1 1 d .
C14 C -0.3073(3) 0.14893(10) -0.3089(2) 0.0416(6) Uani 1 1 d .
C15 C -0.0036(4) 0.27425(12) -0.2519(3) 0.0637(8) Uani 1 1 d .
H15A H 0.0567 0.2650 -0.3038 0.096 Uiso 1 1 calc R
H15B H 0.0592 0.2655 -0.1692 0.096 Uiso 1 1 calc R
H15C H -0.0345 0.3194 -0.2601 0.096 Uiso 1 1 calc R
C16 C -0.2814(3) 0.24913(11) -0.3665(2) 0.0538(7) Uani 1 1 d .
H16 H -0.3031 0.2891 -0.4063 0.065 Uiso 1 1 calc R
C17 C -0.5479(3) 0.20369(13) -0.4598(3) 0.0665(8) Uani 1 1 d .
H17A H -0.6132 0.2097 -0.4104 0.100 Uiso 1 1 calc R
H17B H -0.5764 0.1637 -0.5046 0.100 Uiso 1 1 calc R
H17C H -0.5626 0.2396 -0.5151 0.100 Uiso 1 1 calc R
F1' F 1.011(2) 0.1336(4) 0.349(2) 0.247(6) Uani 0.50 1 d P
F2' F 1.1264(10) 0.2291(5) 0.3689(8) 0.144(5) Uani 0.50 1 d P
F3' F 0.8746(10) 0.2211(11) 0.2679(7) 0.221(6) Uani 0.50 1 d P
F4' F 0.8455(9) 0.2052(8) 0.4450(6) 0.137(4) Uani 0.50 1 d P
F5' F 1.0857(9) 0.1790(10) 0.5251(9) 0.187(5) Uani 0.50 1 d P
F6' F 0.934(2) 0.2619(4) 0.4422(13) 0.212(4) Uani 0.50 1 d P
P1 P 0.98130(10) 0.20038(4) 0.39301(8) 0.0633(3) Uani 1 1 d .
F1 F 0.8760(11) 0.1635(4) 0.2853(6) 0.128(3) Uani 0.50 1 d P
F2 F 0.9219(11) 0.2649(3) 0.3214(9) 0.126(3) Uani 0.50 1 d P
F3 F 1.1126(11) 0.1977(6) 0.3376(10) 0.165(5) Uani 0.50 1 d P
F4 F 1.0474(10) 0.1386(3) 0.4575(9) 0.132(3) Uani 0.50 1 d P
F5 F 0.8425(13) 0.1691(5) 0.4238(12) 0.171(6) Uani 0.50 1 d P
F6 F 1.0892(8) 0.2402(4) 0.5016(6) 0.1148(18) Uani 0.50 1 d P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
H H 0.0000 0.0000 '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
C5 S1 C2 93.35(12)
C8 S2 C11 93.51(12)
C16 N1 C13 108.4(2)
C16 N1 C15 124.4(2)
C13 N1 C15 127.2(2)
C16 N2 C14 108.1(2)
C16 N2 C17 124.7(2)
C14 N2 C17 127.1(2)
C3 C2 C1 128.6(2)
C3 C2 S1 110.08(19)
C1 C2 S1 121.3(2)
C2 C3 C4 113.7(2)
C5 C4 C3 112.8(2)
C5 C4 C13 122.5(2)
C3 C4 C13 124.7(2)
C4 C5 C6 130.4(2)
C4 C5 S1 110.04(18)
C6 C5 S1 119.57(18)
C9 C8 C7 128.5(3)
C9 C8 S2 109.8(2)
C7 C8 S2 121.8(2)
C8 C9 C10 114.1(2)
C11 C10 C9 112.7(2)
C11 C10 C14 123.0(2)
C9 C10 C14 124.2(2)
C10 C11 C12 129.8(2)
C10 C11 S2 109.85(19)
C12 C11 S2 120.38(17)
C14 C13 N1 106.1(2)
C14 C13 C4 130.67(19)
N1 C13 C4 123.0(2)
C13 C14 N2 106.97(19)
C13 C14 C10 131.1(2)
N2 C14 C10 121.8(2)
N1 C16 N2 110.3(2)
F4 F1' F1 115.1(8)
F4 F1' P1 65.3(4)
F1 F1' P1 63.1(4)
F4 F1' F3 93.2(10)
F1 F1' F3 90.9(10)
P1 F1' F3 57.9(4)
F3 F2' P1 75.1(11)
F3 F2' F6 121.3(14)
P1 F2' F6 56.5(4)
F2 F3' F1 136.9(9)
F2 F3' P1 71.2(5)
F1 F3' P1 66.0(5)
F5 F4' F6' 137.1(15)
F5 F4' P1 76.1(12)
F6' F4' P1 61.1(4)
F4 F5' F6 126.5(8)
F4 F5' P1 64.5(5)
F6 F5' P1 64.5(4)
F2 F6' F6 104.0(9)
F2 F6' F4' 102.0(8)
F6 F6' F4' 101.7(7)
F2 F6' P1 65.2(4)
F6 F6' P1 64.0(4)
F4' F6' P1 63.6(4)
F4 P1 F1 91.8(4)
F4 P1 F6' 129.2(6)
F1 P1 F6' 124.1(6)
F4 P1 F1' 47.2(6)
F1 P1 F1' 52.8(7)
F6' P1 F1' 171.7(7)
F4 P1 F3' 137.9(9)
F1 P1 F3' 46.6(7)
F6' P1 F3' 88.1(7)
F1' P1 F3' 92.9(9)
F4 P1 F3 87.1(6)
F1 P1 F3 89.2(6)
F6' P1 F3 123.5(7)
F1' P1 F3 64.8(5)
F3' P1 F3 86.0(5)
F4 P1 F4' 95.1(6)
F1 P1 F4' 90.1(6)
F6' P1 F4' 55.3(5)
F1' P1 F4' 116.4(7)
F3' P1 F4' 91.9(4)
F3 P1 F4' 177.7(6)
F4 P1 F2' 101.4(5)
F1 P1 F2' 111.9(5)
F6' P1 F2' 96.8(7)
F1' P1 F2' 91.5(6)
F3' P1 F2' 91.1(6)
F3 P1 F2' 27.5(6)
F4' P1 F2' 151.7(8)
F4 P1 F6 89.8(4)
F1 P1 F6 178.3(4)
F6' P1 F6 55.0(5)
F1' P1 F6 128.3(8)
F3' P1 F6 131.8(9)
F3 P1 F6 90.3(5)
F4' P1 F6 90.3(5)
F2' P1 F6 67.2(4)
F4 P1 F5 75.4(5)
F1 P1 F5 69.9(6)
F6' P1 F5 84.4(5)
F1' P1 F5 87.3(6)
F3' P1 F5 92.3(7)
F3 P1 F5 151.9(6)
F4' P1 F5 29.1(6)
F2' P1 F5 176.5(6)
F6 P1 F5 111.1(6)
F4 P1 F2 175.8(5)
F1 P1 F2 88.1(3)
F6' P1 F2 53.7(4)
F1' P1 F2 130.5(8)
F3' P1 F2 41.6(7)
F3 P1 F2 88.7(6)
F4' P1 F2 89.1(5)
F2' P1 F2 74.8(5)
F6 P1 F2 90.2(5)
F5 P1 F2 108.5(5)
F4 P1 F5' 42.5(5)
F1 P1 F5' 133.2(7)
F6' P1 F5' 90.5(7)
F1' P1 F5' 88.1(8)
F3' P1 F5' 177.5(4)
F3 P1 F5' 96.5(6)
F4' P1 F5' 85.6(4)
F2' P1 F5' 91.2(5)
F6 P1 F5' 48.5(5)
F5 P1 F5' 85.5(6)
F2 P1 F5' 138.2(8)
F3' F1 F1' 120.1(9)
F3' F1 P1 67.4(5)
F1' F1 P1 64.1(5)
F3' F1 F5 95.6(7)
F1' F1 F5 85.3(8)
P1 F1 F5 56.3(4)
F3' F2 F6' 115.5(10)
F3' F2 P1 67.2(6)
F6' F2 P1 61.1(3)
F2' F3 P1 77.4(13)
F2' F3 F1' 132.4(15)
P1 F3 F1' 57.2(4)
F5' F4 F1' 136.1(10)
F5' F4 P1 72.9(5)
F1' F4 P1 67.5(5)
F4' F5 P1 74.7(12)
F4' F5 F1 111.1(15)
P1 F5 F1 53.8(4)
F5' F6 F6' 108.8(7)
F5' F6 P1 67.0(5)
F6' F6 P1 61.0(4)
F5' F6 F2' 95.3(6)
F6' F6 F2' 93.3(7)
P1 F6 F2' 56.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.720(2)
S1 C2 1.720(3)
S2 C8 1.717(3)
S2 C11 1.722(2)
N1 C16 1.316(3)
N1 C13 1.399(3)
N1 C15 1.470(3)
N2 C16 1.321(3)
N2 C14 1.391(3)
N2 C17 1.458(3)
C1 C2 1.502(4)
C2 C3 1.357(3)
C3 C4 1.426(3)
C4 C5 1.370(3)
C4 C13 1.467(3)
C5 C6 1.492(3)
C7 C8 1.508(4)
C8 C9 1.351(3)
C9 C10 1.425(3)
C10 C11 1.364(3)
C10 C14 1.468(3)
C11 C12 1.496(4)
C13 C14 1.368(3)
F1' F4 1.204(15)
F1' F1 1.343(15)
F1' P1 1.516(6)
F1' F3 1.632(12)
F2' F3 0.730(17)
F2' P1 1.543(8)
F2' F6 1.710(11)
F3' F2 1.095(17)
F3' F1 1.195(18)
F3' P1 1.519(7)
F4' F5 0.778(15)
F4' F6' 1.413(11)
F4' P1 1.541(7)
F5' F4 1.117(14)
F5' F6 1.284(12)
F5' P1 1.579(6)
F6' F2 1.384(11)
F6' F6 1.410(12)
F6' P1 1.505(6)
P1 F4 1.491(5)
P1 F1 1.503(5)
P1 F3 1.528(8)
P1 F6 1.548(4)
P1 F5 1.551(10)
P1 F2 1.560(5)
F1 F5 1.749(14)
