#------------------------------------------------------------------------------
#$Date: 2019-11-04 09:02:49 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222305 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/37/4033730.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_4033730
loop_
_publ_author_name
'Watanabe, Hiroyuki'
'Tanaka, Kazuo'
'Chujo, Yoshiki'
_publ_section_title
;
 Independently Tuned Frontier Orbital Energy Levels of
 1,3,4,6,9b-Pentaazaphenalene Derivatives by the Conjugation Effect.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2768
_journal_page_last               2778
_journal_paper_doi               10.1021/acs.joc.8b03161
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H21 N5'
_chemical_formula_sum            'C16 H21 N5'
_chemical_formula_weight         283.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_Hall           '-C 2c 2'
_space_group_name_H-M_alt        'C m c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.736(4)
_cell_length_b                   8.2462(11)
_cell_length_c                   8.0625(11)
_cell_measurement_reflns_used    3479
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      3.10
_cell_volume                     1511.6(4)
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_collection       'Rigaku RAPID AUTO'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXISIP'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1317
_diffrn_reflns_av_unetI/netI     0.1184
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6785
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         3.585
_diffrn_source                   'sealed Xray tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0767
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
 Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       platelet
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.0767
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1042P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.1899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                648
_reflns_number_total             949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b03161_si_001.cif
_cod_data_source_block           5APtBu
_cod_database_code               4033730
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'-x+1/2, y+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.39524(9) 0.4330(3) 0.2500 0.0289(7) Uani 1 2 d S T P
N2 N 0.5000 0.4293(4) 0.2500 0.0277(8) Uani 1 4 d S T P
N3 N 0.44936(10) 0.6805(3) 0.2500 0.0336(7) Uani 1 2 d S T P
C1 C 0.5000 0.6019(5) 0.2500 0.0291(9) Uani 1 4 d S T P
C2 C 0.5000 0.0970(5) 0.2500 0.0319(10) Uani 1 4 d S T P
C3 C 0.34289(12) 0.6922(3) 0.2500 0.0276(7) Uani 1 2 d S T P
C4 C 0.44631(12) 0.3482(4) 0.2500 0.0298(8) Uani 1 2 d S T P
C5 C 0.39903(12) 0.5934(3) 0.2500 0.0284(7) Uani 1 2 d S T P
C6 C 0.44745(14) 0.1802(4) 0.2500 0.0318(8) Uani 1 2 d S T P
C7 C 0.34288(10) 0.7994(3) 0.4051(3) 0.0320(6) Uani 1 1 d . . .
H7 H 0.3796(10) 0.871(3) 0.409(3) 0.039(6) Uiso 1 1 d . . .
H7A H 0.3430(9) 0.736(2) 0.508(3) 0.033(6) Uiso 1 1 d . . .
C8 C 0.28889(14) 0.5833(4) 0.2500 0.0335(8) Uani 1 2 d S T P
H8 H 0.2874(8) 0.514(3) 0.148(3) 0.037(6) Uiso 1 1 d . . .
H8A H 0.4119(14) 0.131(3) 0.2500 0.031(8) Uiso 1 2 d S . P
H8B H 0.5000 -0.021(6) 0.2500 0.047(14) Uiso 1 4 d S . P
H8C H 0.3073(10) 0.868(2) 0.406(3) 0.032(5) Uiso 1 1 d . . .
H8D H 0.2556(14) 0.644(4) 0.2500 0.038(9) Uiso 1 2 d S . P
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'
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
C5 N1 C4 117.3(2) . .
C4 N2 C4 122.6(3) . 11_655
C4 N2 C1 118.71(17) . .
C4 N2 C1 118.71(17) 11_655 .
C1 N3 C5 118.5(3) . .
N3 C1 N3 121.3(4) 11_655 .
N3 C1 N2 119.36(18) 11_655 .
N3 C1 N2 119.36(18) . .
C6 C2 C6 120.3(4) . 11_655
C6 C2 H8B 119.9(2) . .
C6 C2 H8B 119.9(2) 11_655 .
C5 C3 C8 111.3(3) . .
C5 C3 C7 108.10(16) . .
C8 C3 C7 109.91(17) . .
C5 C3 C7 108.10(16) . 10_556
C8 C3 C7 109.91(17) . 10_556
C7 C3 C7 109.5(2) . 10_556
N1 C4 C6 122.1(3) . .
N1 C4 N2 120.2(3) . .
C6 C4 N2 117.6(3) . .
N1 C5 N3 125.8(3) . .
N1 C5 C3 118.8(2) . .
N3 C5 C3 115.4(2) . .
C2 C6 C4 120.9(3) . .
C2 C6 H8A 123.6(18) . .
C4 C6 H8A 115.4(18) . .
C3 C7 H7 110.8(13) . .
C3 C7 H7A 112.8(12) . .
H7 C7 H7A 106.1(18) . .
C3 C7 H8C 109.6(13) . .
H7 C7 H8C 110.1(18) . .
H7A C7 H8C 107.4(18) . .
C3 C8 H8 111.3(12) . .
C3 C8 H8D 110(2) . .
H8 C8 H8D 106.5(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.325(4) .
N1 C4 1.355(3) .
N2 C4 1.392(3) .
N2 C4 1.392(3) 11_655
N2 C1 1.423(5) .
N3 C1 1.321(3) .
N3 C5 1.351(4) .
C1 N3 1.321(3) 11_655
C2 C6 1.378(4) .
C2 C6 1.378(4) 11_655
C2 H8B 0.97(5) .
C3 C5 1.514(4) .
C3 C8 1.521(4) .
C3 C7 1.531(3) .
C3 C7 1.531(3) 10_556
C4 C6 1.386(4) .
C6 H8A 0.90(3) .
C7 H7 1.02(2) .
C7 H7A 0.98(2) .
C7 H8C 0.99(2) .
C8 H8 1.00(2) .
C8 H8D 0.91(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 N3 C1 N3 180.0 . 11_655
C5 N3 C1 N2 0.0 . .
C4 N2 C1 N3 180.0 . 11_655
C4 N2 C1 N3 0.0 11_655 11_655
C4 N2 C1 N3 0.0 . .
C4 N2 C1 N3 180.0 11_655 .
C5 N1 C4 C6 180.0 . .
C5 N1 C4 N2 0.0 . .
C4 N2 C4 N1 180.0 11_655 .
C1 N2 C4 N1 0.0 . .
C4 N2 C4 C6 0.0 11_655 .
C1 N2 C4 C6 180.0 . .
C4 N1 C5 N3 0.0 . .
C4 N1 C5 C3 180.0 . .
C1 N3 C5 N1 0.0 . .
C1 N3 C5 C3 180.0 . .
C8 C3 C5 N1 0.0 . .
C7 C3 C5 N1 120.79(16) . .
C7 C3 C5 N1 -120.79(16) 10_556 .
C8 C3 C5 N3 180.0 . .
C7 C3 C5 N3 -59.21(16) . .
C7 C3 C5 N3 59.21(16) 10_556 .
C6 C2 C6 C4 0.0 11_655 .
N1 C4 C6 C2 180.0 . .
N2 C4 C6 C2 0.0 . .
loop_
_publcif_info_datablock_id
_publcif_info_datablock_publ_exptl
_publcif_info_datablock_publ_geom
_publcif_info_datablock_structure
{57df45a5-cbb2-492f-872b-faee789d8f8e} y y y
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{57df45a5-cbb2-492f-872b-faee789d8f8e} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{57df45a5-cbb2-492f-872b-faee789d8f8e} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EX
