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_7117690
_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         'C30 H19 N3 O2'
_chemical_formula_sum            'C30 H19 N3 O2'
_chemical_formula_weight         453.48
_chemical_name_systematic        C6-ICor-2CN
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-04-03 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.488(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.2119(4)
_cell_length_b                   21.7175(15)
_cell_length_c                   31.966(2)
_cell_measurement_reflns_used    2820
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.0800
_cell_measurement_theta_min      4.0660
_cell_volume                     4983.7(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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_environment      N~2~
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.867
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -26.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066  -38.0000    0.0000 87

  2 omega   39.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066  178.0000   60.0000 73

  3 omega   47.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066   57.0000  120.0000 53

  4 omega   35.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066  178.0000  -60.0000 54

  5 omega   25.00   73.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -50.0000  120.0000 48

  6 omega   94.00  144.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   38.0000 -180.0000 50

  7 omega   40.00   71.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000  -60.0000 31

  8 omega  141.00  166.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000  -30.0000 25

  9 omega   24.00   50.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -64.0000   30.0000 26

 10 omega   90.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -64.0000   30.0000 26

 11 omega   19.00   45.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000 -120.0000 26

 12 omega   62.00   89.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000 -112.0000 -150.0000 27

 13 omega   94.00  119.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000  120.0000 25

 14 omega   79.00  141.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000   90.0000 62

 15 omega   19.00   72.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000 -180.0000 53

 16 omega   35.00   68.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000  120.0000 33

 17 omega   33.00   59.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000   60.0000 26

 18 omega  107.00  132.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000  -30.0000 25

 19 omega   31.00   70.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000  150.0000 39

 20 omega   24.00   67.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000  -90.0000 43

 21 omega   24.00   85.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -75.0000  -76.0000 61

 22 omega   19.00   72.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000  -30.0000 53

 23 omega  118.00  165.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   25.0000 -120.0000 47

 24 omega   50.00   82.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000 -112.0000  -90.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.0239352000
_diffrn_orient_matrix_UB_12      -0.0425053000
_diffrn_orient_matrix_UB_13      -0.0387905000
_diffrn_orient_matrix_UB_21      -0.2028061000
_diffrn_orient_matrix_UB_22      -0.0128770000
_diffrn_orient_matrix_UB_23      0.0086526000
_diffrn_orient_matrix_UB_31      -0.0654231000
_diffrn_orient_matrix_UB_32      0.0552927000
_diffrn_orient_matrix_UB_33      -0.0277239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_Laue_measured_fraction_full 0.867
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10586
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.146
_diffrn_reflns_theta_min         4.071
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0776
_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^)+(0.1229P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2105
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3070
_reflns_number_total             3918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03550c2.cif
_cod_data_source_block           cr140911a
_cod_database_code               7117690
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 77.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C1(H1A,H1B), C31(H31A,H31B), C41(H41A,H41B), C55(H55A,H55B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C26(H26), C60(H60), C64(H64), C67(H67), C80(H80)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              57486
_shelx_hkl_checksum              59812
_olex2_submission_special_instructions 'No special instructions were received'