Dipolar Second-Order Nonlinear Optical Chromophores Containing Ferrocene, Octamethylferrocene, and Ruthenocene Donors and Strong π-Acceptors: Crystal Structures and Comparison of π-Donor Strengths.
Kinnibrugh, Tiffany L.; Salman, Seyhan; Getmanenko, Yulia A.; Coropceanu, Veaceslav; Porter, 3rd, William W; Timofeeva, Tatiana V.; Matzger, Adam J.; Brédas, Jean-Luc; Marder, Seth R.; Barlow, Stephen; Organometallics 28 (2009) 1350–1357; doi:10.1021/om800986s

data_4068627
_publ_section_title
;
 Dipolar Second-Order Nonlinear Optical Chromophores Containing Ferrocene,
 Octamethylferrocene, and Ruthenocene Donors and Strong \p-Acceptors:
 Crystal Structures and Comparison of \p-Donor Strengths.
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1350
_journal_page_last               1357
_journal_paper_doi               10.1021/om800986s
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C34 H34 Fe N2 O2 S'
_chemical_formula_sum            'C34 H34 Fe N2 O2 S'
_chemical_formula_weight         590.54
_chemical_name_systematic
; 
 (Z)-2-((2E,4E)-5-(2,3,4,5,1',2',3',4'-octamethylferrocen-1-yl)penta-2,4-dienylidene)-3-dicyanomethylidene-2,3-dihydrobenzothiophene-1,1-dioxide 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                94.158(8)
_cell_angle_beta                 95.374(7)
_cell_angle_gamma                99.974(7)
_cell_formula_units_Z            2
_cell_length_a                   8.772(4)
_cell_length_b                   10.597(5)
_cell_length_c                   16.285(8)
_cell_measurement_reflns_used    1941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      2.23
_cell_measurement_theta_min      24.53
_cell_volume                     1478.3(12)
_computing_cell_refinement       'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2  (Bruker, 2005)'
_computing_data_reduction        'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_sigmaI/netI    0.1965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16461
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.393
_refine_diff_density_min         -1.106
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         8149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1666
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0168P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                3776
_reflns_number_total             8149
_reflns_threshold_expression     I&gt;2\s(I)
_cod_data_source_file            om800986s_si_003.cif
_cod_data_source_block           COMPOUND_5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4068627