#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:05:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180168 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/64/7106449.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_7106449
loop_
_publ_author_name
'Md. Minarul Islam'
'Someshwar Pola'
'Yu-Tai Tao'
_publ_section_title
;
 High mobility n-channel single-crystal field-effect transistors based on
 5,7,12,14-tetrachloro-6,13-diazapentacene
;
_journal_name_full               Chem.Commun.
_journal_page_first              6356
_journal_paper_doi               10.1039/c1cc11762a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C10 H4 Cl2 N'
_chemical_formula_sum            'C10 H4 Cl2 N'
_chemical_formula_weight         209.04
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 94.834(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   3.919(5)
_cell_length_b                   12.184(5)
_cell_length_c                   16.985(5)
_cell_measurement_reflns_used    1954
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.41
_cell_volume                     808.1(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5277
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.3737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                1166
_reflns_number_total             1405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11762a.txt
_cod_data_source_block           i10464
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7106449
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.15866(15) 0.91670(5) 0.72308(3) 0.02528(19) Uani 1 1 d . . .
Cl2 Cl 0.42686(16) 0.76881(5) 0.38010(4) 0.0279(2) Uani 1 1 d . . .
N N -0.0645(5) 1.03283(14) 0.57790(11) 0.0177(4) Uani 1 1 d . . .
C1 C 0.2340(5) 0.87364(18) 0.62926(13) 0.0185(5) Uani 1 1 d . . .
C2 C 0.5362(6) 0.70837(18) 0.68340(15) 0.0240(6) Uani 1 1 d . . .
H2 H 0.4982 0.7290 0.7346 0.029 Uiso 1 1 calc R . .
C3 C 0.7091(6) 0.61435(18) 0.67128(16) 0.0273(6) Uani 1 1 d . . .
H3 H 0.7920 0.5721 0.7143 0.033 Uiso 1 1 calc R . .
C4 C 0.7650(6) 0.57984(18) 0.59389(16) 0.0280(6) Uani 1 1 d . . .
H4 H 0.8807 0.5144 0.5866 0.034 Uiso 1 1 calc R . .
C5 C 0.6520(6) 0.64098(18) 0.53000(16) 0.0246(6) Uani 1 1 d . . .
H5 H 0.6914 0.6169 0.4796 0.030 Uiso 1 1 calc R . .
C6 C 0.3565(6) 0.80775(17) 0.47515(14) 0.0202(5) Uani 1 1 d . . .
C7 C 0.1104(5) 0.94011(17) 0.56461(13) 0.0176(5) Uani 1 1 d . . .
C8 C 0.1747(5) 0.90702(16) 0.48529(14) 0.0179(5) Uani 1 1 d . . .
C9 C 0.4111(6) 0.77645(17) 0.61845(14) 0.0198(5) Uani 1 1 d . . .
C10 C 0.4724(5) 0.74226(17) 0.53941(14) 0.0194(5) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0305(3) 0.0297(3) 0.0158(3) -0.0005(2) 0.0024(3) 0.0000(2)
Cl2 0.0328(4) 0.0312(3) 0.0197(4) -0.0060(3) 0.0032(3) 0.0057(2)
N 0.0173(9) 0.0196(9) 0.0162(10) -0.0004(8) 0.0010(8) -0.0029(7)
C1 0.0176(11) 0.0221(11) 0.0159(13) -0.0003(10) 0.0018(10) -0.0052(9)
C2 0.0225(12) 0.0273(12) 0.0220(14) 0.0049(11) 0.0011(11) -0.0050(9)
C3 0.0213(12) 0.0249(12) 0.0353(16) 0.0126(12) -0.0004(12) -0.0035(10)
C4 0.0233(12) 0.0205(12) 0.0404(17) 0.0020(11) 0.0038(12) 0.0015(9)
C5 0.0226(12) 0.0212(11) 0.0302(15) -0.0034(11) 0.0038(11) -0.0017(9)
C6 0.0198(11) 0.0218(11) 0.0192(13) -0.0041(10) 0.0040(10) -0.0037(9)
C7 0.0158(11) 0.0191(10) 0.0178(12) -0.0004(10) 0.0009(10) -0.0039(9)
C8 0.0159(11) 0.0195(11) 0.0183(13) -0.0019(10) 0.0022(10) -0.0047(9)
C9 0.0164(11) 0.0211(11) 0.0220(13) 0.0022(10) 0.0014(10) -0.0055(9)
C10 0.0169(11) 0.0189(10) 0.0222(13) -0.0022(10) 0.0009(10) -0.0044(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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
_geom_angle_publ_flag
C8 N C7 117.22(19) 3_576 . ?
C9 C1 C7 121.7(2) . . ?
C9 C1 Cl1 120.39(18) . . ?
C7 C1 Cl1 117.90(17) . . ?
C3 C2 C9 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C9 C2 H2 119.5 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C10 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C10 C5 H5 119.6 . . ?
C10 C6 C8 121.6(2) . . ?
C10 C6 Cl2 120.43(17) . . ?
C8 C6 Cl2 117.91(17) . . ?
N C7 C1 119.6(2) . . ?
N C7 C8 121.3(2) . . ?
C1 C7 C8 119.14(19) . . ?
N C8 C6 119.9(2) 3_576 . ?
N C8 C7 121.53(19) 3_576 . ?
C6 C8 C7 118.5(2) . . ?
C1 C9 C2 122.2(2) . . ?
C1 C9 C10 119.4(2) . . ?
C2 C9 C10 118.4(2) . . ?
C6 C10 C5 122.3(2) . . ?
C6 C10 C9 119.51(19) . . ?
C5 C10 C9 118.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.727(2) . ?
Cl2 C6 1.727(2) . ?
N C8 1.341(3) 3_576 ?
N C7 1.350(3) . ?
C1 C9 1.392(3) . ?
C1 C7 1.416(3) . ?
C2 C3 1.355(3) . ?
C2 C9 1.433(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.415(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.436(3) . ?
C5 H5 0.9300 . ?
C6 C10 1.397(3) . ?
C6 C8 1.422(3) . ?
C7 C8 1.449(3) . ?
C8 N 1.341(3) 3_576 ?
C9 C10 1.445(3) . ?
