#------------------------------------------------------------------------------
#$Date: 2019-07-17 10:24:38 +0300 (Wed, 17 Jul 2019) $
#$Revision: 217111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233179.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7233179
loop_
_publ_author_name
'Miriam Mas-Montoya'
'Rocio Ponce Ortiz'
'David Curiel'
'Arturo Espinosa'
'Magali Allain'
'Antonio Facchetti'
'Tobin J. Marks'
_publ_section_title
;
 Isomeric carbazolocarbazoles: synthesis, characterization and comparative
 study in Organic Field Effect Transistors
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1959
_journal_page_last               1969
_journal_paper_doi               10.1039/C2TC00363E
_journal_volume                  1
_journal_year                    2013
_chemical_formula_moiety         'C38 H46 N2'
_chemical_formula_sum            'C38 H46 N2'
_chemical_formula_weight         530.77
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 96.53(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.341(3)
_cell_length_b                   12.123(1)
_cell_length_c                   8.5232(8)
_cell_measurement_reflns_used    4237
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.67
_cell_volume                     1574.9(4)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.2f (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12476
_diffrn_reflns_theta_full        27.6
_diffrn_reflns_theta_max         27.6
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'(SADABS (Sheldrick, Bruker, 2000))'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_gt           0.0761
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+1.2158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1873
_reflns_number_gt                1913
_reflns_number_total             3573
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_cod_database_code               7233179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.33696(18) 0.5234(2) 0.3563(3) 0.0476(7) Uani 1 d . . .
C2 C 0.2690(2) 0.5508(2) 0.4443(4) 0.0577(8) Uani 1 d . . .
H2 H 0.2642 0.5174 0.5412 0.069 Uiso 1 calc R . .
C3 C 0.2093(2) 0.6284(3) 0.3841(4) 0.0641(9) Uani 1 d . . .
H3 H 0.1628 0.6467 0.4403 0.077 Uiso 1 calc R . .
C4 C 0.2169(2) 0.6804(3) 0.2401(4) 0.0668(9) Uani 1 d . . .
H4 H 0.176 0.7334 0.2024 0.08 Uiso 1 calc R . .
C5 C 0.28429(19) 0.6540(2) 0.1533(4) 0.0558(8) Uani 1 d . . .
H5 H 0.289 0.6897 0.058 0.067 Uiso 1 calc R . .
C6 C 0.34597(17) 0.5735(2) 0.2083(3) 0.0438(6) Uani 1 d . . .
C7 C 0.42172(17) 0.5230(2) 0.1504(3) 0.0416(6) Uani 1 d . . .
C8 C 0.45480(17) 0.4467(2) 0.2664(3) 0.0432(6) Uani 1 d . . .
C9 C 0.46244(16) 0.5335(2) 0.0082(3) 0.0412(6) Uani 1 d . . .
C10 C 0.43050(18) 0.6069(2) -0.1159(3) 0.0472(7) Uani 1 d . . .
H10 H 0.3809 0.649 -0.1048 0.057 Uiso 1 calc R . .
C11 C 0.47026(17) 0.6176(2) -0.2507(3) 0.0479(7) Uani 1 d . . .
H11 H 0.4483 0.6661 -0.3301 0.057 Uiso 1 calc R . .
C12 C 0.4112(2) 0.3684(2) 0.5197(3) 0.0532(7) Uani 1 d . . .
H12A H 0.3813 0.3979 0.6049 0.064 Uiso 1 calc R . .
H12B H 0.4726 0.3592 0.5593 0.064 Uiso 1 calc R . .
C13 C 0.3727(2) 0.2566(2) 0.4732(4) 0.0561(8) Uani 1 d . . .
H13A H 0.4047 0.2264 0.3913 0.067 Uiso 1 calc R . .
H13B H 0.3826 0.2081 0.5639 0.067 Uiso 1 calc R . .
C14 C 0.2760(2) 0.2542(2) 0.4143(4) 0.0595(8) Uani 1 d . . .
H14A H 0.2663 0.2938 0.3149 0.071 Uiso 1 calc R . .
H14B H 0.2436 0.2918 0.4897 0.071 Uiso 1 calc R . .
C15 C 0.2414(2) 0.1373(3) 0.3906(4) 0.0693(9) Uani 1 d . . .
H15A H 0.2754 0.0996 0.3176 0.083 Uiso 1 calc R . .
H15B H 0.2507 0.0986 0.4908 0.083 Uiso 1 calc R . .
C16 C 0.1468(2) 0.1301(3) 0.3293(5) 0.0797(11) Uani 1 d . . .
H16A H 0.1381 0.1659 0.2269 0.096 Uiso 1 calc R . .
H16B H 0.1132 0.1706 0.3998 0.096 Uiso 1 calc R . .
C17 C 0.1107(3) 0.0122(3) 0.3120(6) 0.0928(13) Uani 1 d . . .
H17A H 0.1436 -0.0283 0.2403 0.111 Uiso 1 calc R . .
H17B H 0.1196 -0.0241 0.414 0.111 Uiso 1 calc R . .
C18 C 0.0165(3) 0.0075(5) 0.2526(8) 0.1310(19) Uani 1 d . . .
H18A H 0.0075 0.0438 0.1506 0.157 Uiso 1 calc R . .
H18B H -0.0164 0.0481 0.3244 0.157 Uiso 1 calc R . .
C19 C -0.0195(4) -0.1089(5) 0.2355(9) 0.163(3) Uani 1 d . . .
H19A H 0.004 -0.1449 0.1491 0.245 Uiso 1 calc R . .
H19B H -0.0823 -0.1063 0.2153 0.245 Uiso 1 calc R . .
H19C H -0.0029 -0.1492 0.3311 0.245 Uiso 1 calc R . .
N1 N 0.40415(15) 0.44749(18) 0.3902(3) 0.0482(6) Uani 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 129.1(3) . .
N1 C1 C6 108.9(2) . .
C2 C1 C6 122.1(3) . .
C3 C2 C1 118.1(3) . .
C3 C2 H2 120.9 . .
C1 C2 H2 120.9 . .
C2 C3 C4 121.3(3) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C5 C4 C3 120.7(3) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 120.1(3) . .
C4 C5 H5 120 . .
C6 C5 H5 120 . .
C5 C6 C1 117.7(3) . .
C5 C6 C7 135.8(3) . .
C1 C6 C7 106.5(2) . .
C8 C7 C9 119.8(2) . .
C8 C7 C6 106.1(2) . .
C9 C7 C6 134.0(2) . .
N1 C8 C7 110.1(2) . .
N1 C8 C11 127.9(2) . 3_665
C7 C8 C11 122.0(2) . 3_665
C10 C9 C9 119.7(3) . 3_665
C10 C9 C7 122.5(2) . .
C9 C9 C7 117.8(3) 3_665 .
C11 C10 C9 122.3(2) . .
C11 C10 H10 118.9 . .
C9 C10 H10 118.9 . .
C10 C11 C8 118.4(2) . 3_665
C10 C11 H11 120.8 . .
C8 C11 H11 120.8 3_665 .
N1 C12 C13 113.4(2) . .
N1 C12 H12A 108.9 . .
C13 C12 H12A 108.9 . .
N1 C12 H12B 108.9 . .
C13 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C14 C13 C12 116.3(3) . .
C14 C13 H13A 108.2 . .
C12 C13 H13A 108.2 . .
C14 C13 H13B 108.2 . .
C12 C13 H13B 108.2 . .
H13A C13 H13B 107.4 . .
C13 C14 C15 112.1(3) . .
C13 C14 H14A 109.2 . .
C15 C14 H14A 109.2 . .
C13 C14 H14B 109.2 . .
C15 C14 H14B 109.2 . .
H14A C14 H14B 107.9 . .
C16 C15 C14 114.4(3) . .
C16 C15 H15A 108.7 . .
C14 C15 H15A 108.7 . .
C16 C15 H15B 108.7 . .
C14 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
C15 C16 C17 114.6(3) . .
C15 C16 H16A 108.6 . .
C17 C16 H16A 108.6 . .
C15 C16 H16B 108.6 . .
C17 C16 H16B 108.6 . .
H16A C16 H16B 107.6 . .
C18 C17 C16 113.5(4) . .
C18 C17 H17A 108.9 . .
C16 C17 H17A 108.9 . .
C18 C17 H17B 108.9 . .
C16 C17 H17B 108.9 . .
H17A C17 H17B 107.7 . .
C17 C18 C19 113.6(5) . .
C17 C18 H18A 108.8 . .
C19 C18 H18A 108.8 . .
C17 C18 H18B 108.8 . .
C19 C18 H18B 108.8 . .
H18A C18 H18B 107.7 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C8 N1 C1 108.4(2) . .
C8 N1 C12 125.1(2) . .
C1 N1 C12 125.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.388(3) .
C1 C2 1.392(4) .
C1 C6 1.420(4) .
C2 C3 1.371(4) .
C2 H2 0.93 .
C3 C4 1.397(5) .
C3 H3 0.93 .
C4 C5 1.375(4) .
C4 H4 0.93 .
C5 C6 1.403(4) .
C5 H5 0.93 .
C6 C7 1.449(4) .
C7 C8 1.406(4) .
C7 C9 1.431(4) .
C8 N1 1.380(3) .
C8 C11 1.408(4) 3_665
C9 C10 1.426(3) .
C9 C9 1.430(5) 3_665
C10 C11 1.366(4) .
C10 H10 0.93 .
C11 C8 1.408(4) 3_665
C11 H11 0.93 .
C12 N1 1.458(3) .
C12 C13 1.513(4) .
C12 H12A 0.97 .
C12 H12B 0.97 .
C13 C14 1.511(4) .
C13 H13A 0.97 .
C13 H13B 0.97 .
C14 C15 1.519(4) .
C14 H14A 0.97 .
C14 H14B 0.97 .
C15 C16 1.488(5) .
C15 H15A 0.97 .
C15 H15B 0.97 .
C16 C17 1.534(5) .
C16 H16A 0.97 .
C16 H16B 0.97 .
C17 C18 1.477(6) .
C17 H17A 0.97 .
C17 H17B 0.97 .
C18 C19 1.516(6) .
C18 H18A 0.97 .
C18 H18B 0.97 .
C19 H19A 0.96 .
C19 H19B 0.96 .
C19 H19C 0.96 .
