A bowl-shaped molecule for organic field-effect transistors: crystal engineering and charge transport switching by oxygen doping
Shi, Ke; Lei, Ting; Wang, Xiao-Ye; Wang, Jie-Yu; Pei, Jian; Chemical Science 5 (2014) 1041–; doi:10.1039/c3sc52701h

data_1513693
_publ_section_title
;
 A bowl-shaped molecule for organic field-effect transistors: crystal
 engineering and charge transport switching by oxygen doping
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              1041
_journal_paper_doi               10.1039/c3sc52701h
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C38 H29 N O2'
_chemical_formula_sum            'C38 H29 N O2'
_chemical_formula_weight         531.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                95.055(3)
_cell_angle_beta                 95.380(4)
_cell_angle_gamma                95.045(3)
_cell_formula_units_Z            4
_cell_length_a                   7.2711(3)
_cell_length_b                   11.9307(5)
_cell_length_c                   29.9623(13)
_cell_measurement_reflns_used    5060
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.2280
_cell_measurement_theta_min      3.5900
_cell_volume                     2565.54(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9660
_diffrn_measured_fraction_theta_max 0.7751
_diffrn_measurement_details
;
  1 omega  -81.00   98.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        8.8364    0.0000  -30.0000 179

  2 omega  -14.00   36.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.6957 -106.0000  123.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0178512000
_diffrn_orient_matrix_UB_12      0.0098750000
_diffrn_orient_matrix_UB_13      -0.0229331000
_diffrn_orient_matrix_UB_21      0.0953798000
_diffrn_orient_matrix_UB_22      -0.0024369000
_diffrn_orient_matrix_UB_23      -0.0028264000
_diffrn_orient_matrix_UB_31      -0.0166058000
_diffrn_orient_matrix_UB_32      -0.0590975000
_diffrn_orient_matrix_UB_33      -0.0060708000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14297
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.27
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         9387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+1.4134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                6878
_reflns_number_total             9387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc52701h.txt
_cod_data_source_block           exp_1104
_cod_original_cell_volume        2565.55(19)
_cod_database_code               1513693
_chemical_oxdiff_formula         C38H29NO2
_chemical_oxdiff_usercomment     CI-1
_reflns_odcompleteness_completeness 96.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H18 of C18, H19 of C19, H20 of C20, H21 of C21, {H36A,H36B} of C36, H11 of
  C11, H12 of C12, H14 of C14, H15 of C15, {H37A,H37B} of C37, {H33A,H33B} of
  C33, H43 of C43, H5 of C5, H6 of C6, H7 of C7, H8 of C8, {H31A,H31B} of C31,
  H49 of C49, {H74A,H74B} of C74, {H75A,H75B} of C75, H58 of C58, H59 of C59,
  {H69A,H69B} of C69, {H70A,H70B} of C70, {H71A,H71B} of C71, {H72A,H72B} of
  C72, {H73A,H73B} of C73, H44 of C44, {H34A,H34B} of C34, H57 of C57, H50 of
  C50, H56 of C56, H45 of C45, {H32A,H32B} of C32, {H35A,H35B} of C35, H52 of
  C52, H53 of C53, H46 of C46
 At 1.5 times of:
  {H76A,H76B,H76C} of C76, {H38A,H38B,H38C} of C38
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C69(H69A,H69B), C70(H70A,H70B),
 C71(H71A,H71B), C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C43(H43), C44(H44), C45(H45), C46(H46),
  C49(H49), C50(H50), C52(H52), C53(H53), C56(H56), C57(H57), C58(H58), C59(H59)
2.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C76(H76A,H76B,H76C)
;