Croconaines as molecular materials for organic electronics: synthesis, solid state structure and use in transistor devices
A. Punzi; M. A. M. Capozzi; V. Fino; C. Carlucci; M. Suriano; E. Mesto; E. Schingaro; E. Orgiu; S. Bonacchi; T. Leydecker; P. Samori; R. Musio; G. M. Farinola; Journal of Materials Chemistry C 4 (2016) 3138–3142; doi:10.1039/C6TC00264A

data_7234659
_publ_section_title
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 Croconaines as molecular materials for organic electronics: synthesis,
 solid state structure and use in transistor devices
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_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3138
_journal_page_last               3142
_journal_paper_doi               10.1039/C6TC00264A
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C27 H22 Br2 N2 O3'
_chemical_formula_sum            'C27 H22 Br2 N2 O3'
_chemical_formula_weight         582.29
_chemical_name_systematic
;      
3-[(5-Bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)methyl]-5-
[(5-bromo-3,3-dimethyl-3H-indol-2-yl)methylene]-4-hydroxy-3-5
cyclopentene-1,2-dione
;
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 103.0900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8186(2)
_cell_length_b                   10.0198(2)
_cell_length_c                   23.1493(5)
_cell_measurement_reflns_used    9024
_cell_measurement_temperature    293
_cell_measurement_theta_max      35
_cell_measurement_theta_min      2
_cell_volume                     2444.18(9)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'Apex2 (Bruker AXS, 2010)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mecrury (Macrae et al., 2008)'
_computing_publication_material  CRYSTALS
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27449
_diffrn_reflns_theta_full        23.279
_diffrn_reflns_theta_max         23.279
_diffrn_reflns_theta_min         1.806
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.349
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platly
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9696
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.0004246
_refine_ls_shift/su_mean         0.0000159
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 6.75P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0914
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0914
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                2536
_reflns_number_total             3509
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.05
_oxford_diffrn_Wilson_scale      45.05
_oxford_refine_ls_r_factor_ref   0.0647
_oxford_refine_ls_scale          0.16233(8)
_oxford_reflns_number_all        3491
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3138.cif
_cod_data_source_block           S27_4b
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               7234659
_iucr_refine_instruction_details_constraints
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BLOCK SCALE X'S, U'S 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE N   (   2,X'S) H   (  21,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 153,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 273,X'S) H   ( 271,X'S) 
END                                                                             
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