A simple route to phosphamethine cyanines from S,N-heterocyclic carbenes.
Binder, Justin F.; Corrente, Andrea M.; Macdonald, Charles L. B.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 2138–2147; doi:10.1039/c5dt03019f

data_7036983
_publ_section_title
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 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 S4, I'
_chemical_formula_sum            'C14 H22 I N2 P S4'
_chemical_formula_weight         504.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     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                 103.289(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8142(7)
_cell_length_b                   7.1440(4)
_cell_length_c                   24.3816(13)
_cell_measurement_reflns_used    9760
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      38.52
_cell_measurement_theta_min      2.98
_cell_volume                     2002.7(2)
_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      173.2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            94035
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         38.653
_diffrn_reflns_theta_min         2.978
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.094
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0572 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9081.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.094
_refine_diff_density_max         1.440
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         11356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+1.5227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9058
_reflns_number_total             11356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt03019f2.cif
_cod_data_source_block           jb208s2
_cod_depositor_comments
'Adding full bibliography for 7036976--7036983.cif.'
_cod_database_code               7036983
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.828
_shelx_estimated_absorpt_t_min   0.672
_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:
 C151(H15A,H15B), C251(H25A,H25B)
2.b Idealised Me refined as rotating group:
 C141(H14A,H14B,H14C), C231(H23A,H23B,H23C), C241(H24A,H24B,H24C), C131(H13A,
 H13B,H13C), C252(H25C,H25D,H25E), C152(H15C,H15D,H15E)
;
_olex2_submission_special_instructions 'No special instructions were received'