#------------------------------------------------------------------------------
#$Date: 2016-02-05 02:10:51 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176081 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/69/7036982.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_7036982
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         'C14 H22 N2 P S2, I'
_chemical_formula_sum            'C14 H22 I N2 P S2'
_chemical_formula_weight         440.32
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2015-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.4096(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6665(7)
_cell_length_b                   10.2797(5)
_cell_length_c                   13.4062(7)
_cell_measurement_reflns_used    9143
_cell_measurement_temperature    173.19
_cell_measurement_theta_max      30.33
_cell_measurement_theta_min      3.16
_cell_volume                     1777.80(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.19
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.556
_diffrn_reflns_theta_min         3.158
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.119
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0615 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9354.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear reddish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0193P)²+1.4287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0429
_refine_ls_wR_factor_ref         0.0455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2352
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt03019f2.cif
_cod_data_source_block           mo_jb187_0m
_cod_depositor_comments
'Adding full bibliography for 7036976--7036983.cif.'
_cod_original_cell_volume        1777.80(15)
_cod_database_code               7036982
_shelxl_version_number           2013-4
_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_max   0.909
_shelx_estimated_absorpt_t_min   0.810
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B)
2.b Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C41(H41A,H41B,H41C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.5000 0.61786(2) 0.2500 0.02640(5) Uani 1 2 d S T P
S2 S 0.42589(3) -0.04456(4) 0.12666(3) 0.01764(8) Uani 1 1 d . . .
P1 P 0.5000 0.22908(6) 0.2500 0.02028(12) Uani 1 2 d S T P
C1 C 0.44825(11) 0.11997(14) 0.13207(12) 0.0157(3) Uani 1 1 d . . .
C52 C 0.33134(15) 0.38594(18) -0.02385(18) 0.0342(4) Uani 1 1 d . . .
H52A H 0.2703 0.3489 -0.0886 0.051 Uiso 1 1 calc GR . .
H52B H 0.3427 0.4748 -0.0421 0.051 Uiso 1 1 calc GR . .
H52C H 0.3201 0.3875 0.0426 0.051 Uiso 1 1 calc GR . .
C41 C 0.31080(14) 0.11214(19) -0.18351(14) 0.0291(4) Uani 1 1 d . . .
H41A H 0.2448 0.1549 -0.2027 0.044 Uiso 1 1 calc GR . .
H41B H 0.2979 0.0344 -0.2307 0.044 Uiso 1 1 calc GR . .
H41C H 0.3555 0.1722 -0.1973 0.044 Uiso 1 1 calc GR . .
N5 N 0.41256(10) 0.16616(13) 0.02508(10) 0.0174(2) Uani 1 1 d . . .
C51 C 0.42540(13) 0.30348(16) 0.00161(14) 0.0224(3) Uani 1 1 d . . .
H51A H 0.4391 0.3072 -0.0639 0.027 Uiso 1 1 calc R . .
H51B H 0.4865 0.3403 0.0681 0.027 Uiso 1 1 calc R . .
C31 C 0.31942(13) -0.17007(18) -0.08385(15) 0.0275(4) Uani 1 1 d . . .
H31A H 0.3431 -0.2436 -0.0310 0.041 Uiso 1 1 calc GR . .
H31B H 0.3418 -0.1825 -0.1414 0.041 Uiso 1 1 calc GR . .
H31C H 0.2436 -0.1650 -0.1208 0.041 Uiso 1 1 calc GR . .
C3 C 0.36499(12) -0.04639(16) -0.02018(13) 0.0189(3) Uani 1 1 d . . .
C4 C 0.36320(12) 0.07362(16) -0.06084(13) 0.0193(3) 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'
P P 0.1023 0.0942 '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_3
C1 S2 C3 92.49(7) .
C1 P1 C1 102.23(10) 2_655
S2 C1 P1 130.36(9) .
N5 C1 S2 109.27(11) .
N5 C1 P1 120.23(11) .
H52A C52 H52B 109.5 .
H52A C52 H52C 109.5 .
H52B C52 H52C 109.5 .
C51 C52 H52A 109.5 .
C51 C52 H52B 109.5 .
C51 C52 H52C 109.5 .
H41A C41 H41B 109.5 .
H41A C41 H41C 109.5 .
H41B C41 H41C 109.5 .
C4 C41 H41A 109.5 .
C4 C41 H41B 109.5 .
C4 C41 H41C 109.5 .
C1 N5 C51 122.34(13) .
C1 N5 C4 114.83(13) .
C4 N5 C51 122.82(13) .
C52 C51 H51A 109.0 .
C52 C51 H51B 109.0 .
N5 C51 C52 112.85(14) .
N5 C51 H51A 109.0 .
N5 C51 H51B 109.0 .
H51A C51 H51B 107.8 .
H31A C31 H31B 109.5 .
H31A C31 H31C 109.5 .
H31B C31 H31C 109.5 .
C3 C31 H31A 109.5 .
C3 C31 H31B 109.5 .
C3 C31 H31C 109.5 .
C31 C3 S2 120.35(13) .
C4 C3 S2 110.55(12) .
C4 C3 C31 129.05(15) .
N5 C4 C41 121.14(15) .
C3 C4 C41 126.02(15) .
C3 C4 N5 112.78(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S2 C1 1.7177(15) .
S2 C3 1.7322(15) .
P1 C1 1.7866(15) .
P1 C1 1.7866(15) 2_655
C1 N5 1.3573(18) .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
C52 C51 1.513(2) .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
C41 C4 1.500(2) .
N5 C51 1.478(2) .
N5 C4 1.401(2) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C31 C3 1.500(2) .
C3 C4 1.344(2) .
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_site_symmetry_1
S2 C1 N5 C51 -176.69(11) .
S2 C1 N5 C4 3.08(16) .
S2 C3 C4 C41 -175.54(13) .
S2 C3 C4 N5 1.47(17) .
P1 C1 N5 C51 7.22(19) .
P1 C1 N5 C4 -173.01(10) .
C1 S2 C3 C31 -177.35(13) .
C1 S2 C3 C4 0.21(13) .
C1 P1 C1 S2 12.94(7) 2_655
C1 P1 C1 N5 -171.91(15) 2_655
C1 N5 C51 C52 -95.78(18) .
C1 N5 C4 C41 174.14(14) .
C1 N5 C4 C3 -3.04(19) .
C51 N5 C4 C41 -6.1(2) .
C51 N5 C4 C3 176.73(14) .
C31 C3 C4 C41 1.8(3) .
C31 C3 C4 N5 178.77(15) .
C3 S2 C1 P1 173.71(11) .
C3 S2 C1 N5 -1.85(11) .
C4 N5 C51 C52 84.47(18) .
