#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/56/1505613.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_1505613
loop_
_publ_author_name
'Kamplain, Justin W.'
'Lynch, Vincent M.'
'Bielawski, Christopher W.'
_publ_section_title
;
 Synthesis and study of differentially substituted
 dibenzotetraazafulvalenes.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5401
_journal_page_last               5404
_journal_paper_doi               10.1021/ol702230r
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C20 H18 N4 Br4, C6 H6'
_chemical_formula_sum            'C26 H24 Br4 N4'
_chemical_formula_weight         712.13
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 114.053(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.2572(4)
_cell_length_b                   7.5300(2)
_cell_length_c                   17.5917(5)
_cell_measurement_reflns_used    3086
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     2571.34(12)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω-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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5019
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    6.283
_exptl_absorpt_correction_T_max  0.575
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.991
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.096
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0527P)²+11.6226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                2260
_reflns_number_total             2946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702230r-file003.cif
_cod_data_source_block           brbridge
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2571.34(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1505613
loop_
_symmetry_equiv_pos_as_xyz
'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, -y, -z'
'x, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33539(3) 0.31310(9) -0.18604(4) 0.0681(3) Uani 1 1 d . . .
Br2 Br 0.50363(4) 0.24945(10) -0.14712(4) 0.0707(3) Uani 1 1 d . . .
N1 N 0.4248(3) 0.3013(6) 0.1442(3) 0.0572(11) Uani 1 1 d . . .
N2 N 0.5379(3) 0.2553(6) 0.1700(3) 0.0614(12) Uani 1 1 d . . .
C1 C 0.4920(4) 0.2784(7) 0.2089(3) 0.0634(15) Uani 1 1 d . . .
C2 C 0.4317(3) 0.2933(6) 0.0684(3) 0.0503(12) Uani 1 1 d . . .
C3 C 0.3823(3) 0.3105(7) -0.0107(3) 0.0499(11) Uani 1 1 d . . .
H3 H 0.3355 0.3324 -0.0213 0.060 Uiso 1 1 calc R . .
C4 C 0.4044(3) 0.2942(7) -0.0765(3) 0.0503(11) Uani 1 1 d . . .
C5 C 0.4722(3) 0.2651(7) -0.0607(3) 0.0513(12) Uani 1 1 d . . .
C6 C 0.5220(3) 0.2510(7) 0.0204(3) 0.0549(12) Uani 1 1 d . . .
H6 H 0.5691 0.2328 0.0313 0.066 Uiso 1 1 calc R . .
C7 C 0.5007(3) 0.2644(7) 0.0843(3) 0.0518(12) Uani 1 1 d . . .
C8 C 0.3738(3) 0.4183(8) 0.1539(4) 0.0686(16) Uani 1 1 d . . .
H8A H 0.3597 0.5069 0.1109 0.103 Uiso 1 1 d R . .
H8B H 0.3938 0.4748 0.2074 0.103 Uiso 1 1 d R . .
H8C H 0.3345 0.3498 0.1500 0.103 Uiso 0.50 1 d PR . .
C9 C 0.5992(4) 0.1435(10) 0.2056(4) 0.097(3) Uani 1 1 d D . .
H9A H 0.5994 0.0548 0.1665 0.145 Uiso 1 1 d R . .
H9B H 0.5908 0.0865 0.2494 0.145 Uiso 1 1 d R . .
H9C H 0.6406 0.2134 0.2263 0.145 Uiso 0.50 1 d PR . .
C10 C 0.6596(5) 0.2228(12) 0.2473(6) 0.045(2) Uani 0.50 1 d PD . .
H10A H 0.6589 0.3117 0.2079 0.054 Uiso 0.50 1 d PR . .
H10B H 0.6958 0.1406 0.2530 0.054 Uiso 0.50 1 d PR . .
C11 C 0.6734(5) 0.3157(14) 0.3311(7) 0.053(2) Uani 0.50 1 d PD . .
H11A H 0.7135 0.3877 0.3423 0.064 Uiso 0.50 1 d PR . .
H11B H 0.6867 0.2237 0.3725 0.064 Uiso 0.50 1 d PR . .
C1A C 0.7359(11) 0.176(3) -0.0786(10) 0.062(3) Uani 0.56 1 d PU . 1
H1AA H 0.7288 0.1355 -0.1333 0.074 Uiso 0.56 1 d PR . 1
C2A C 0.7850(9) 0.313(3) -0.0436(14) 0.055(3) Uani 0.56 1 d PU A 1
H2AA H 0.8130 0.3589 -0.0702 0.066 Uiso 0.56 1 d PR A 1
C3A C 0.7995(9) 0.387(2) 0.0345(15) 0.065(4) Uani 0.56 1 d PU . 1
H3AA H 0.8314 0.4824 0.0585 0.078 Uiso 0.56 1 d PR . 1
C1B C 0.7676(19) 0.249(5) -0.0670(18) 0.075(6) Uani 0.44 1 d PU . 2
H1BA H 0.7828 0.2606 -0.1112 0.090 Uiso 0.44 1 d PR . 2
C2B C 0.7998(12) 0.358(3) 0.000(3) 0.069(5) Uani 0.44 1 d PU B 2
H2BA H 0.8373 0.4363 0.0063 0.082 Uiso 0.44 1 d PR B 2
C3B C 0.7839(17) 0.363(5) 0.066(2) 0.090(9) Uani 0.44 1 d PU . 2
H3BA H 0.8036 0.4375 0.1140 0.108 Uiso 0.44 1 d PR . 2
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'
Br Br -0.2901 2.4595 '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
C2 N1 C1 107.2(5) . .
C2 N1 C8 120.5(5) . .
C1 N1 C8 121.9(5) . .
C7 N2 C1 108.6(5) . .
C7 N2 C9 120.5(4) . .
C1 N2 C9 122.3(5) . .
C1 C1 N2 126.7(9) 2_655 .
C1 C1 N1 126.2(8) 2_655 .
N2 C1 N1 107.0(4) . .
C3 C2 C7 121.8(5) . .
C3 C2 N1 129.2(5) . .
C7 C2 N1 109.0(5) . .
C2 C3 C4 116.9(5) . .
C2 C3 H3 121.6 . .
C4 C3 H3 121.6 . .
C5 C4 C3 121.2(5) . .
C5 C4 Br1 122.3(4) . .
C3 C4 Br1 116.6(4) . .
C4 C5 C6 121.2(5) . .
C4 C5 Br2 122.1(4) . .
C6 C5 Br2 116.6(4) . .
C7 C6 C5 117.8(5) . .
C7 C6 H6 121.1 . .
C5 C6 H6 121.1 . .
C6 C7 N2 130.6(5) . .
C6 C7 C2 121.2(5) . .
N2 C7 C2 108.2(5) . .
C11 C8 N1 108.5(6) 2_655 .
N1 C8 H8A 109.6 . .
N1 C8 H8B 109.2 . .
H8A C8 H8B 109.6 . .
N1 C8 H8C 109.4 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 N2 117.9(7) . .
C10 C9 H9A 115.0 . .
N2 C9 H9A 110.9 . .
C10 C9 H9B 102.1 . .
N2 C9 H9B 100.1 . .
H9A C9 H9B 108.7 . .
N2 C9 H9C 111.5 . .
H9A C9 H9C 112.5 . .
H9B C9 H9C 112.5 . .
C9 C10 C11 119.6(8) . .
C9 C10 H10A 100.7 . .
C11 C10 H10A 108.3 . .
C9 C10 H10B 108.6 . .
C11 C10 H10B 111.1 . .
H9C C10 H10B 114.6 . .
H10A C10 H10B 107.5 . .
C8 C11 C10 124.5(8) 2_655 .
C8 C11 H11A 107.4 2_655 .
C10 C11 H11A 105.0 . .
C8 C11 H11B 105.8 2_655 .
C10 C11 H11B 106.2 . .
H11A C11 H11B 106.8 . .
C3A C1A C2A 118.8(14) 7_655 .
C3A C1A H1AA 124.2 7_655 .
C2A C1A H1AA 117.0 . .
C3A C2A C1A 123.2(15) . .
C3A C2A H2AA 113.7 . .
C1A C2A H2AA 123.0 . .
C1A C3A C2A 118.0(16) 7_655 .
C1A C3A H3AA 117.5 7_655 .
C2A C3A H3AA 124.5 . .
H2BA C3A H3BA 124.0 . .
C2B C1B C3B 118(2) . 7_655
H1AA C1B H2AA 123.3 . .
C2B C1B H1BA 115.3 . .
C3B C1B H1BA 126.5 7_655 .
C3B C2B C1B 123(2) . .
H2AA C2B H3AA 117.7 . .
C3B C2B H2BA 111.5 . .
C2B C3B C1B 118(3) . 7_655
C2B C3B H3BA 128.0 . .
C1B C3B H3BA 113.6 7_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.892(5) .
Br2 C5 1.897(5) .
N1 C2 1.400(6) .
N1 C1 1.428(8) .
N1 C8 1.460(7) .
N2 C7 1.390(7) .
N2 C1 1.414(8) .
N2 C9 1.461(8) .
C1 C1 1.343(10) 2_655
C2 C3 1.365(7) .
C2 C7 1.395(8) .
C3 C4 1.420(7) .
C3 H3 0.95 .
C4 C5 1.371(8) .
C5 C6 1.391(8) .
C6 C7 1.376(7) .
C6 H6 0.95 .
C8 C11 1.375(10) 2_655
C8 H8A 0.96 .
C8 H8B 0.96 .
C8 H8C 0.96 .
C9 C10 1.332(10) .
C9 H9A 0.96 .
C9 H9B 0.96 .
C9 H9C 0.96 .
C10 C11 1.547(14) .
C10 H10A 0.96 .
C10 H10B 0.96 .
C11 C8 1.374(10) 2_655
C11 H11A 0.96 .
C11 H11B 0.96 .
C1A C3A 1.37(2) 7_655
C1A C2A 1.42(2) .
C1A H1AA 0.96 .
C2A C3A 1.396(19) .
C2A H2AA 0.96 .
C3A C1A 1.37(2) 7_655
C3A H3AA 0.96 .
C1B C2B 1.36(3) .
C1B C3B 1.39(3) 7_655
C1B H1BA 0.96 .
C2B C3B 1.33(3) .
C2B H2BA 0.9601 .
C3B C1B 1.39(3) 7_655
C3B H3BA 0.96 .
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
C7 N2 C1 C1 -179.9(3) . 2_655
C9 N2 C1 C1 32.2(7) . 2_655
C7 N2 C1 N1 0.3(6) . .
C9 N2 C1 N1 -147.6(6) . .
C2 N1 C1 C1 179.6(3) . 2_655
C8 N1 C1 C1 34.7(6) . 2_655
C2 N1 C1 N2 -0.5(6) . .
C8 N1 C1 N2 -145.5(5) . .
C1 N1 C2 C3 -179.0(5) . .
C8 N1 C2 C3 -33.5(8) . .
C1 N1 C2 C7 0.6(6) . .
C8 N1 C2 C7 146.2(5) . .
C7 C2 C3 C4 1.2(7) . .
N1 C2 C3 C4 -179.3(5) . .
C2 C3 C4 C5 -0.9(7) . .
C2 C3 C4 Br1 178.7(4) . .
C3 C4 C5 C6 -0.2(8) . .
Br1 C4 C5 C6 -179.8(4) . .
C3 C4 C5 Br2 -178.2(4) . .
Br1 C4 C5 Br2 2.3(6) . .
C4 C5 C6 C7 1.0(8) . .
Br2 C5 C6 C7 179.1(4) . .
C5 C6 C7 N2 179.8(5) . .
C5 C6 C7 C2 -0.8(8) . .
C1 N2 C7 C6 179.6(6) . .
C9 N2 C7 C6 -31.8(10) . .
C1 N2 C7 C2 0.1(6) . .
C9 N2 C7 C2 148.7(6) . .
C3 C2 C7 C6 -0.3(8) . .
N1 C2 C7 C6 -180.0(5) . .
C3 C2 C7 N2 179.2(5) . .
N1 C2 C7 N2 -0.5(6) . .
C2 N1 C8 C11 116.5(7) . 2_655
C1 N1 C8 C11 -103.1(8) . 2_655
C7 N2 C9 C10 116.0(8) . .
C1 N2 C9 C10 -99.8(10) . .
N2 C9 C10 C11 67.5(12) . .
C9 C10 C11 C8 -41.5(15) . 2_655
C3A C1A C2A C3A 1(2) 7_655 .
C1A C2A C3A C1A -1(2) . 7_655
C3B C1B C2B C3B -1(4) 7_655 .
C1B C2B C3B C1B 1(4) . 7_655
