Corannulene derivatives with low LUMO levels and dense convex-concave packing for n-channel organic field-effect transistors
Rui Chen; Ru-Qiang Lu; Ke Shi; Fan Wu; Hong-Xun Fang; Zhe-Xuan Niu; Xiao-Yun Yan; Ming Luo; Xin-Chang Wang; Chi-Yuan Yang; Xiao-Ye Wang; Binbin Xu; Haiping Xia; Jian Pei; Xiao-Yu Cao; Chem.Commun. 51 (2015) 13768–; doi:10.1039/C5cc03550C

data_7117689
_publ_section_title
;
 Corannulene derivatives with low LUMO levels and dense convex-concave
 packing for n-channel organic field-effect transistors
;
_journal_name_full               Chem.Commun.
_journal_page_first              13768
_journal_paper_doi               10.1039/C5cc03550C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C32 H23 N3 O2'
_chemical_formula_sum            'C32 H23 N3 O2'
_chemical_formula_weight         481.53
_chemical_name_systematic        EH-ICor-2CN
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-04-03 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.946(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.040(3)
_cell_length_b                   21.8380(18)
_cell_length_c                   7.2037(7)
_cell_measurement_temperature    173(2)
_cell_volume                     5169.7(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12299
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.813
_diffrn_reflns_theta_min         2.995
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       needle
_exptl_crystal_F_000             2016
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.462
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1949
_refine_ls_R_factor_gt           0.1191
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1981P)^2^+4.3275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3431
_refine_ls_wR_factor_ref         0.3910
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3242
_reflns_number_total             5844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03550c2.cif
_cod_data_source_block           1
_cod_original_cell_volume        5169.8(8)
_cod_database_code               7117689
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C1A)
Uanis(C6) = Uanis(C2A)
3. Others
 Sof(H49A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(H49)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(1)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(2)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C49(H49), C49(H49A)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C18(H18A,H18B), C52(H52A,H52B), C5(H5A,H5B),
 C1A(H1AA,H1AB)
4.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C32(H32), C46(H46), C55(H55), C8(H8), C66(H66)
4.d Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C6(H6A,H6B,H6C), C2A(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              11860
_shelx_hkl_checksum              15401