#------------------------------------------------------------------------------
#$Date: 2016-02-05 02:10:51 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176081 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/69/7036976.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_7036976
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         'C6 H10 N S, I'
_chemical_formula_sum            'C6 H10 I N S'
_chemical_formula_weight         255.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_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                 92.1710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5748(2)
_cell_length_b                   7.6434(2)
_cell_length_c                   13.3454(3)
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      62.33
_cell_measurement_theta_min      3.57
_cell_volume                     874.04(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker PHOTON 100 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16440
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.072
_exptl_absorpt_coefficient_mu    3.824
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2014'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.278
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0242
_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)+(0.0400P)²+0.2902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0665
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1975
_reflns_number_total             1997
_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               7036976
_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.
;
_shelx_estimated_absorpt_t_min   0.385
_shelx_estimated_absorpt_t_max   0.617
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.2110(2) 1.0691(3) 0.18778(15) 0.0202(4) Uani 1 1 d . .
H1 H 0.130(3) 1.0620(4) 0.1448(15) 0.024 Uiso 1 1 calc R U
C3 C 0.3451(2) 1.1257(2) 0.33540(14) 0.0173(4) Uani 1 1 d . .
C4 C 0.4627(2) 1.0655(2) 0.27993(13) 0.0173(3) Uani 1 1 d . .
C21 C 0.0565(3) 1.1831(3) 0.32518(19) 0.0287(5) Uani 1 1 d . .
H21A H -0.0284 1.1785 0.2740 0.043 Uiso 1 1 calc R U
H21B H 0.0678 1.3030 0.3503 0.043 Uiso 1 1 calc R U
H21C H 0.0324 1.1048 0.3807 0.043 Uiso 1 1 calc R U
C31 C 0.3518(3) 1.1854(3) 0.44182(17) 0.0229(4) Uani 1 1 d . .
H31A H 0.4598 1.1803 0.4683 0.034 Uiso 1 1 calc R U
H31B H 0.2863 1.1091 0.4817 0.034 Uiso 1 1 calc R U
H31C H 0.3135 1.3060 0.4454 0.034 Uiso 1 1 calc R U
C41 C 0.6295(2) 1.0357(3) 0.31035(15) 0.0225(4) Uani 1 1 d . .
H41A H 0.6584 1.1112 0.3674 0.034 Uiso 1 1 calc R U
H41B H 0.6954 1.0634 0.2540 0.034 Uiso 1 1 calc R U
H41C H 0.6446 0.9129 0.3296 0.034 Uiso 1 1 calc R U
N N 0.2033(2) 1.1272(2) 0.28090(12) 0.0185(3) Uani 1 1 d . .
S S 0.39355(6) 1.01038(7) 0.16051(3) 0.02096(12) Uani 1 1 d . .
I I 0.18590(2) 0.69733(2) 0.44106(2) 0.02182(9) 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 111.90(15)
N C1 H1 124.0
S C1 H1 124.0
C4 C3 N 111.77(17)
C4 C3 C31 128.47(19)
N C3 C31 119.77(18)
C3 C4 C41 129.09(17)
C3 C4 S 110.45(15)
C41 C4 S 120.38(14)
N C21 H21A 109.5
N C21 H21B 109.5
H21A C21 H21B 109.5
N 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
C1 N C3 114.44(17)
C1 N C21 123.20(18)
C3 N C21 122.33(17)
C1 S C4 91.44(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N 1.324(3)
C1 S 1.681(2)
C1 H1 0.89(3)
C3 C4 1.355(3)
C3 N 1.393(3)
C3 C31 1.491(3)
C4 C41 1.489(3)
C4 S 1.7313(19)
C21 N 1.474(3)
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_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
C1 H1 I 0.89 3.08 3.881(2) 151.5 2
C21 H21A I 0.98 3.13 4.049(3) 157.1 2
C31 H31B I 0.98 3.30 3.992(2) 129.0 .
C31 H31C I 0.98 3.19 4.163(2) 176.1 1_565
C41 H41A I 0.98 3.19 4.157(2) 167.9 3_676
C41 H41B I 0.98 3.01 3.961(2) 163.7 2_655
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
N C3 C4 C41 -177.05(19)
C31 C3 C4 C41 2.5(3)
N C3 C4 S -0.3(2)
C31 C3 C4 S 179.24(16)
S C1 N C3 -0.5(2)
S C1 N C21 -178.41(16)
C4 C3 N C1 0.6(2)
C31 C3 N C1 -179.07(18)
C4 C3 N C21 178.48(19)
C31 C3 N C21 -1.1(3)
N C1 S C4 0.24(16)
C3 C4 S C1 0.07(16)
C41 C4 S C1 177.10(17)
