#------------------------------------------------------------------------------
#$Date: 2016-02-05 02:10:51 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176081 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/69/7036977.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_7036977
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         'C7 H12 N S, I'
_chemical_formula_sum            'C7 H12 I N S'
_chemical_formula_weight         269.14
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2014/7
_audit_update_record
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                78.7720(10)
_cell_angle_beta                 82.5190(10)
_cell_angle_gamma                73.7020(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2083(10)
_cell_length_b                   8.0237(11)
_cell_length_c                   8.8800(12)
_cell_measurement_reflns_used    4598
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.35
_cell_volume                     481.96(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.970
_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  0.0213
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_laue_measured_fraction_full 0.997
_diffrn_reflns_laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5441
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.346
_exptl_absorpt_coefficient_mu    3.473
_exptl_absorpt_correction_T_max  0.249
_exptl_absorpt_correction_T_min  0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2001'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blob
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0207
_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)+(0.0232P)²+0.0704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2032
_reflns_number_total             2144
_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               7036977
_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, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C -0.1281(3) 0.3478(3) 0.3132(3) 0.0256(5) Uani 1 1 d . .
H1 H -0.219(3) 0.3888(13) 0.391(2) 0.031 Uiso 1 1 calc R U
N N 0.0602(3) 0.2884(2) 0.3287(2) 0.0226(4) Uani 1 1 d . .
S S -0.18366(8) 0.34034(8) 0.13709(7) 0.02779(13) Uani 1 1 d . .
C3 C 0.1699(3) 0.2347(3) 0.1976(3) 0.0231(5) Uani 1 1 d . .
C4 C 0.0572(3) 0.2501(3) 0.0823(3) 0.0248(5) Uani 1 1 d . .
C20 C 0.1439(3) 0.2725(3) 0.4766(3) 0.0266(5) Uani 1 1 d . .
H20A H 0.0534(18) 0.3405(14) 0.5405(13) 0.032 Uiso 1 1 calc R U
H20B H 0.253(2) 0.3162(9) 0.4577(4) 0.032 Uiso 1 1 calc R U
C21 C 0.1999(4) 0.0839(3) 0.5575(3) 0.0342(6) Uani 1 1 d . .
H21A H 0.0826 0.0440 0.5931 0.051 Uiso 1 1 calc R U
H21B H 0.2719 0.0759 0.6460 0.051 Uiso 1 1 calc R U
H21C H 0.2814 0.0094 0.4859 0.051 Uiso 1 1 calc R U
C31 C 0.3854(3) 0.1718(3) 0.1898(3) 0.0303(5) Uani 1 1 d . .
H31A H 0.4240 0.0449 0.2280 0.046 Uiso 1 1 calc R U
H31B H 0.4356 0.2336 0.2536 0.046 Uiso 1 1 calc R U
H31C H 0.4383 0.1955 0.0828 0.046 Uiso 1 1 calc R U
C41 C 0.1215(4) 0.1977(4) -0.0718(3) 0.0337(6) Uani 1 1 d . .
H41A H 0.2319 0.2443 -0.1173 0.051 Uiso 1 1 calc R U
H41B H 0.0146 0.2452 -0.1389 0.051 Uiso 1 1 calc R U
H41C H 0.1605 0.0689 -0.0608 0.051 Uiso 1 1 calc R U
I I 0.37362(2) 0.66638(2) 0.27089(2) 0.03061(7) 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'
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
N C1 S 112.21(18)
N C1 H1 123.9
S C1 H1 123.9
C1 N C3 114.2(2)
C1 N C20 122.31(19)
C3 N C20 123.41(19)
C1 S C4 91.16(11)
C4 C3 N 111.7(2)
C4 C3 C31 126.0(2)
N C3 C31 122.2(2)
C3 C4 C41 127.2(2)
C3 C4 S 110.63(17)
C41 C4 S 122.18(18)
N C20 C21 111.74(19)
N C20 H20A 109.3
C21 C20 H20A 109.3
N C20 H20B 109.3
C21 C20 H20B 109.3
H20A C20 H20B 107.9
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
C1 N 1.322(3)
C1 S 1.680(2)
C1 H1 0.93(3)
N C3 1.390(3)
N C20 1.484(3)
S C4 1.728(2)
C3 C4 1.354(3)
C3 C31 1.489(3)
C4 C41 1.489(3)
C20 C21 1.510(3)
C20 H20A 0.932(18)
C20 H20B 0.932(18)
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
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
S C1 N C3 0.4(2)
S C1 N C20 -176.54(16)
N C1 S C4 0.88(18)
C1 N C3 C4 -2.0(3)
C20 N C3 C4 175.0(2)
C1 N C3 C31 177.1(2)
C20 N C3 C31 -6.0(3)
N C3 C4 C41 -176.8(2)
C31 C3 C4 C41 4.2(4)
N C3 C4 S 2.5(2)
C31 C3 C4 S -176.46(19)
C1 S C4 C3 -1.97(18)
C1 S C4 C41 177.4(2)
C1 N C20 C21 103.6(2)
C3 N C20 C21 -73.1(3)
