#------------------------------------------------------------------------------
#$Date: 2016-02-05 02:10:51 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176081 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/69/7036978.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_7036978
loop_
_publ_author_name
'Binder, Justin F.'
'Corrente, Andrea M.'
'Macdonald, Charles L. B.'
_publ_section_title
;
 A simple route to phosphamethine cyanines from S,N-heterocyclic carbenes.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2138
_journal_page_last               2147
_journal_paper_doi               10.1039/c5dt03019f
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C8 H14 N S, I'
_chemical_formula_sum            'C8 H14 I N S'
_chemical_formula_weight         283.16
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0281(14)
_cell_length_b                   7.7753(9)
_cell_length_c                   11.5619(13)
_cell_measurement_reflns_used    7067
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.44
_cell_volume                     1081.3(2)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11622
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.234
_diffrn_reflns_theta_min         2.443
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_T_max  0.538
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2001'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0220P)²+1.0142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1261
_reflns_number_total             1386
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt03019f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7036976--7036983.cif.'
_cod_database_code               7036978
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.2031(3) 0.2500 0.6331(3) 0.0414(10) Uani 1 2 d S T P
N N 0.2741(2) 0.2500 0.5467(2) 0.0292(6) Uani 1 2 d S T P
S S 0.07033(7) 0.2500 0.58936(8) 0.0402(2) Uani 1 2 d S T P
C3 C 0.2230(3) 0.2500 0.4383(3) 0.0246(6) Uani 1 2 d S T P
C4 C 0.1110(3) 0.2500 0.4467(3) 0.0262(7) Uani 1 2 d S T P
C20 C 0.3967(3) 0.2500 0.5680(3) 0.0325(8) Uani 1 2 d S T P
C21 C 0.4293(2) 0.0887(4) 0.6325(2) 0.0397(6) Uani 1 1 d . . .
H21A H 0.3979 0.0920 0.7106 0.059 Uiso 1 1 calc R U .
H21B H 0.5106 0.0817 0.6374 0.059 Uiso 1 1 calc R U .
H21C H 0.4008 -0.0122 0.5913 0.059 Uiso 1 1 calc R U .
C31 C 0.2911(3) 0.2500 0.3312(3) 0.0356(8) Uani 1 2 d S T P
H31A H 0.3319 0.1412 0.3253 0.053 Uiso 0.5 1 calc R U P
H31B H 0.3440 0.3458 0.3337 0.053 Uiso 0.5 1 calc R U P
H31C H 0.2424 0.2630 0.2638 0.053 Uiso 0.5 1 calc R U P
C41 C 0.0265(3) 0.2500 0.3525(3) 0.0345(8) Uani 1 2 d S T P
H41A H 0.0603 0.2069 0.2810 0.052 Uiso 0.5 1 calc R U P
H41B H -0.0006 0.3675 0.3402 0.052 Uiso 0.5 1 calc R U P
H41C H -0.0359 0.1756 0.3744 0.052 Uiso 0.5 1 calc R U P
H20 H 0.433(3) 0.2500 0.487(4) 0.041(11) Uiso 1 2 d S . P
H1 H 0.221(3) 0.2500 0.707(4) 0.040(12) Uiso 1 2 d S . P
I I 0.26044(2) 0.2500 0.95317(2) 0.03314(9) Uani 1 2 d S T P
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'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N C1 S 113.0(3) . .
N C1 H1 125(3) . .
S C1 H1 122(3) . .
C1 N C3 113.3(3) . .
C1 N C20 121.1(3) . .
C3 N C20 125.6(3) . .
C1 S C4 91.04(18) . .
C4 C3 N 112.0(3) . .
C4 C3 C31 127.6(3) . .
N C3 C31 120.4(3) . .
C3 C4 C41 128.9(3) . .
C3 C4 S 110.6(2) . .
C41 C4 S 120.4(3) . .
N C20 C21 109.72(18) . .
N C20 C21 109.72(18) . 8_565
C21 C20 C21 112.2(3) . 8_565
N C20 H20 106(2) . .
C21 C20 H20 109.7(11) . .
C21 C20 H20 109.7(11) 8_565 .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C3 C31 H31A 109.5 . .
C3 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C3 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C4 C41 H41A 109.5 . .
C4 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
C4 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N 1.314(5) .
C1 S 1.675(4) .
C1 H1 0.88(4) .
N C3 1.396(4) .
N C20 1.495(4) .
S C4 1.720(3) .
C3 C4 1.350(5) .
C3 C31 1.485(4) .
C4 C41 1.490(4) .
C20 C21 1.511(3) .
C20 C21 1.511(3) 8_565
C20 H20 1.03(4) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
