Bowl shaped deformation in a planar aromatic polycycle upon reduction. Li and Na separated dianions of the aromatic polycycle 5,6:11,12-di-o-phenylene-tetracene
Schneider, Joerg J.; Wombacher, Tobias; Goddard, Richard; Lehmann, Christian W.; Dalton Trans.  (2017) –; doi:10.1039/C7DT03039H

data_7044149
_publ_section_title
;
 Bowl shaped deformation in a planar aromatic polycycle upon reduction. Li
 and Na separated dianions of the aromatic polycycle
 5,6:11,12-di-o-phenylene-tetracene
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT03039H
_journal_year                    2017
_chemical_compound_source        diglyme
_chemical_formula_moiety         'C30 H16, 2(C12 H28 Na O6)'
_chemical_formula_sum            'C54 H72 Na2 O12'
_chemical_formula_weight         959.09
_chemical_name_systematic
'5,6:11,12-di-o-phenylenetetracene tetra(diglyme)disodium'
_chemical_properties_physical
', Air-sensitive,Moisture-sensitive,Heat-sensitive,Oxygen-sensitive'
_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_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                DOPT/Na/Diglyme/10106/100K
_audit_creation_date             2016-06-08
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-06 deposited with the CCDC.
2017-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.704(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.101(2)
_cell_length_b                   13.542(2)
_cell_length_c                   15.849(3)
_cell_measurement_reflns_used    9372
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.9291
_cell_measurement_theta_min      2.2887
_cell_volume                     2533.6(7)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         'Incoatec I\mS micro-focus X-ray source'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            256525
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.597
_diffrn_reflns_theta_min         2.635
_diffrn_source                   I\mS
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.96625
_exptl_absorpt_correction_T_min  0.94331
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.614
_exptl_crystal_size_mid          0.593
_exptl_crystal_size_min          0.533
_refine_diff_density_max         1.090
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         13081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+1.1582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10334
_reflns_number_total             13081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03039h2.cif
_cod_data_source_block           3
_cod_original_cell_volume        2533.7(8)
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'p 21/n'
_cod_database_code               7044149
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              78458