Syntheses and Properties of Two-Dimensional, Dicationic Nonlinear Optical Chromophores Based on Pyrazinyl Cores
Benjamin J. Coe; John Fielden; Simon P. Foxon; Madeleine Helliwell; Inge Asselberghs; Koen Clays; Kurt De Mey; Bruce S. Brunschwig; Journal of Organic Chemistry 75 (2010) 8550–8563; doi:10.1021/jo101966r

data_4025908
_publ_contact_author_address
;
School of Chemistry, University of Manchester, Oxford Road, Manchester, M13
 9PL, UK.
;
_publ_contact_author_email       b.coe@manchester.ac.uk
_publ_contact_author_name        'Benjamin J. Coe'
_publ_section_title
;
 Syntheses and Properties of Two-Dimensional, Dicationic Nonlinear Optical
 Chromophores Based on Pyrazinyl Cores
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8550
_journal_page_last               8563
_journal_paper_doi               10.1021/jo101966r
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C32 H28 N4 O2, C2 H3 N, 2(F6 P)'
_chemical_formula_sum            'C34 H31 F12 N5 O2 P2'
_chemical_formula_weight         831.58
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   8.050(1)
_cell_length_b                   39.185(11)
_cell_length_c                   11.293(2)
_cell_measurement_reflns_used    1526
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4160
_cell_measurement_theta_min      2.7285
_cell_volume                     3562.3(13)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04) 
;
_computing_molecular_graphics    'SHELXTL (Bruker, 1997'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_sigmaI/netI    0.1076
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5666
_diffrn_reflns_theta_full        21.95
_diffrn_reflns_theta_max         21.95
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0966
_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^)+(0.0913P)^2^+19.1497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2354
_reflns_number_gt                1402
_reflns_number_total             2199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101966r_si_001.1.cif
_cod_data_source_block           '[6][NO3]2.MeCN'
_cod_original_cell_volume        3562.3(12)
_cod_database_code               4025908