#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:41:05 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178911 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/40/4114098.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_4114098
loop_
_publ_author_name
'Qian Miao'
'Thuc-Quyen Nguyen'
'Takao Someya'
'Graciela B. Blanchet'
'Colin Nuckolls'
_publ_section_title
;
 Synthesis, Assembly, and Thin Film Transistors of Dihydrodiazapentacene:
 An Isostructural Motif for Pentacene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10284
_journal_page_last               10287
_journal_paper_doi               10.1021/ja036466+
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C26 H28 N4 O2'
_chemical_formula_weight         428.52
_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                90.00
_cell_angle_beta                 99.767(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.1863(5)
_cell_length_b                   17.0800(16)
_cell_length_c                   10.7410(10)
_cell_measurement_temperature    243(2)
_cell_volume                     1118.47(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      243(2)
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.890
_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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7206
_diffrn_reflns_theta_full        28.06
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9523
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.003(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0484
_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)+(0.1500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1729
_refine_ls_wR_factor_ref         0.1900
_reflns_number_gt                1922
_reflns_number_total             2420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0364662Bsi20030602_100256.cif
_cod_data_source_block           greens2
_cod_database_code               4114098
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
N N 0.17178(17) 0.49667(7) 0.93412(10) 0.0436(4) Uani 1 1 d .
H0A H 0.2802 0.4944 0.8921 0.052 Uiso 1 1 calc R
C1 C 0.4524(2) 0.21430(9) 1.27421(15) 0.0526(4) Uani 1 1 d .
H1A H 0.5622 0.1762 1.2948 0.063 Uiso 1 1 calc R
C2 C 0.4675(2) 0.26849(8) 1.18157(14) 0.0473(4) Uani 1 1 d .
H2A H 0.5883 0.2669 1.1391 0.057 Uiso 1 1 calc R
C3 C 0.3052(2) 0.32643(8) 1.14896(12) 0.0383(4) Uani 1 1 d .
C4 C 0.31695(19) 0.38362(7) 1.05405(12) 0.0383(4) Uani 1 1 d .
H4A H 0.4352 0.3824 1.0095 0.046 Uiso 1 1 calc R
C5 C 0.16060(19) 0.44027(7) 1.02612(11) 0.0347(3) Uani 1 1 d .
C6 C 0.01943(19) 0.55625(7) 0.90575(11) 0.0346(3) Uani 1 1 d .
C7 C 0.03513(19) 0.61112(7) 0.81458(11) 0.0378(4) Uani 1 1 d .
H7A H 0.1545 0.6090 0.7710 0.045 Uiso 1 1 calc R
C8 C -0.1240(2) 0.67093(8) 0.78432(12) 0.0383(4) Uani 1 1 d .
C9 C -0.1117(2) 0.72844(8) 0.69053(13) 0.0476(4) Uani 1 1 d .
H9A H 0.0086 0.7284 0.6475 0.057 Uiso 1 1 calc R
C10 C -0.2716(3) 0.78390(9) 0.66163(15) 0.0533(4) Uani 1 1 d .
H10A H -0.2610 0.8211 0.5985 0.064 Uiso 1 1 calc R
O1S O 0.37885(19) 0.44882(8) 0.73541(11) 0.0686(4) Uani 1 1 d .
N1S N 0.61503(17) 0.42490(7) 0.60116(10) 0.0412(3) Uani 1 1 d .
C1S C 0.5531(3) 0.46120(9) 0.69781(14) 0.0515(4) Uani 1 1 d .
H1SA H 0.6483 0.4990 0.7408 0.062 Uiso 1 1 calc R
C2S C 0.8236(3) 0.44320(11) 0.56237(18) 0.0647(5) Uani 1 1 d .
H2SA H 0.8969 0.4843 0.6160 0.097 Uiso 1 1 calc R
H2SB H 0.7977 0.4608 0.4752 0.097 Uiso 1 1 calc R
H2SC H 0.9151 0.3968 0.5700 0.097 Uiso 1 1 calc R
C3S C 0.4807(3) 0.36510(10) 0.53211(15) 0.0588(5) Uani 1 1 d .
H3SA H 0.3388 0.3639 0.5591 0.088 Uiso 1 1 calc R
H3SB H 0.5518 0.3146 0.5483 0.088 Uiso 1 1 calc R
H3SC H 0.4610 0.3765 0.4424 0.088 Uiso 1 1 calc R
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 0.0000 0.0000 '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'
O O 0.0106 0.0060 '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_3
C6 N C5 123.46(11) .
C2 C1 C10 119.76(13) 3_567
C1 C2 C3 121.30(13) .
C2 C3 C4 122.61(12) .
C2 C3 C8 118.88(12) 3_567
C4 C3 C8 118.50(12) 3_567
C5 C4 C3 121.58(12) .
C4 C5 N 121.91(11) .
C4 C5 C6 120.00(12) 3_567
N C5 C6 118.08(11) 3_567
C7 C6 N 122.09(11) .
C7 C6 C5 119.44(12) 3_567
N C6 C5 118.46(11) 3_567
C6 C7 C8 121.72(11) .
C7 C8 C9 122.88(12) .
C7 C8 C3 118.73(12) 3_567
C9 C8 C3 118.38(12) 3_567
C10 C9 C8 121.14(13) .
C9 C10 C1 120.51(13) 3_567
C1S N1S C3S 121.25(12) .
C1S N1S C2S 120.90(13) .
C3S N1S C2S 117.84(13) .
O1S C1S N1S 124.31(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N C6 1.3854(17) .
N C5 1.3901(17) .
C1 C2 1.374(2) .
C1 C10 1.410(2) 3_567
C2 C3 1.4107(19) .
C3 C4 1.4227(19) .
C3 C8 1.4299(18) 3_567
C4 C5 1.3651(18) .
C5 C6 1.4338(17) 3_567
C6 C7 1.3707(18) .
C6 C5 1.4338(17) 3_567
C7 C8 1.4178(18) .
C8 C9 1.4184(19) .
C8 C3 1.4299(18) 3_567
C9 C10 1.367(2) .
C10 C1 1.410(2) 3_567
O1S C1S 1.2320(18) .
N1S C1S 1.3206(19) .
N1S C3S 1.4404(19) .
N1S C2S 1.4553(17) .
