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_7234660
_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 H24 N2 O3'
_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_weight         424.50
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_cell_angle_alpha                66.188(2)
_cell_angle_beta                 81.891(2)
_cell_angle_gamma                72.294(2)
_cell_formula_units_Z            4
_cell_length_a                   11.0823(3)
_cell_length_b                   14.6505(5)
_cell_length_c                   18.1033(6)
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    293
_cell_measurement_theta_max      32
_cell_measurement_theta_min      2
_cell_volume                     2561.12(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'Apex2 (Bruker AXS, 2010)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'MERCURY (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 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5370
_diffrn_reflns_theta_full        20.464
_diffrn_reflns_theta_max         20.882
_diffrn_reflns_theta_min         1.579
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platly
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.0001964
_refine_ls_shift/su_mean         0.0000176
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 1.34P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1601
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1601
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3300
_reflns_number_total             5370
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.08
_oxford_diffrn_Wilson_scale      12.04
_oxford_refine_ls_r_factor_ref   0.1105
_oxford_refine_ls_scale          0.4039(8)
_oxford_reflns_number_all        5331
_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           S41_4a
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7234660
_iucr_refine_instruction_details_constraints
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BLOCK SCALE X'S, U'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   (  13,X'S) H   ( 131,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   ( 161,X'S) H   ( 163,X'S) H   ( 162,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   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) H   ( 273,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 423,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 433,X'S) H   ( 432,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 533,X'S) H   ( 532,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 543,X'S) H   ( 542,X'S) 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE N   (   2,X'S) H   (  21,X'S) 
RIDE N   (   3,X'S) H   (  31,X'S) 
RIDE N   (   4,X'S) H   (  41,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
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SIMU  C(51)  C(50)  AND C(61)  C(60) 
DELU  C(51)  C(50)  AND C(61)  C(60) 
SIMU  0.005 C(36)  C(41)  AND C(47)  C(52) 
DELU  0.005 C(36)  C(41)  AND C(47)  C(52) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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