Aromaticity of an Unsaturated N-Heterocyclic Stannylene (HCRN)2SnIIAs Studied by Optical Spectra and Quantum Chemistry. Comparison in the Series (HCRN)2EII, E = C, Si, Ge, Sn (R =t-Bu or Dip)
Leites, Larissa A.; Bukalov, Sergey S.; Aysin, Rinat R.; Piskunov, Alexander V.; Chegerev, Maxim G.; Cherkasov, Vladimir K.; Zabula, Alexander V.; West, Robert; Organometallics 34 (2015) 2278–; doi:10.1021/om501054t

data_4085575
_publ_section_title
;
 Aromaticity of an Unsaturated N-Heterocyclic Stannylene (HCRN)2SnIIAs
 Studied by Optical Spectra and Quantum Chemistry. Comparison in the
 Series (HCRN)2EII, E = C, Si, Ge, Sn (R =t-Bu or Dip)
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2278
_journal_paper_doi               10.1021/om501054t
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C26 H36 N2 Sn'
_chemical_formula_sum            'C26 H36 N2 Sn'
_chemical_formula_weight         495.26
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.047(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.996(6)
_cell_length_b                   6.518(2)
_cell_length_c                   20.004(5)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.563
_cell_measurement_theta_min      2.602
_cell_volume                     2539.9(13)
_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  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.1
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22365
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.63
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1263 before and 0.0357 after correction.
The Ratio of minimum to maximum transmission is 0.8749.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.136
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+4.8284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                3493
_reflns_number_total             3884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om501054t_si_003.cif
_cod_data_source_block           west370
_cod_depositor_comments          'Adding full bibliography for 4085575.cif.'
_cod_original_cell_volume        2540.0(13)
_cod_database_code               4085575
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C12 \\sim C14A-C12 \\sim C13A-C12 \\sim C13-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C13) = Uanis(C13A)
Uanis(C14A) = Uanis(C14)
4. Others
 Sof(H12A)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C13A)=Sof(H13D)=
 Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(H12)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 Sof(H14C)=FVAR(1)
 Fixed Sof: Sn1(0.5) C1(0.5) H1(0.5) C2(0.5) H2(0.5)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12), C12(H12A)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C14A(H14D,H14E,H14F), C13A(H13D,H13E,H13F)
;
_olex2_submission_special_instructions 'No special instructions were received'