#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:00:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180164 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/60/7106081.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_7106081
loop_
_publ_author_name
'Bin Yan'
'Jordan Cramen'
'Robert McDonald'
'Natia L. Frank'
_publ_section_title
;
 Ferromagnetic Spin-Delocalized Electron Donors for Multifunctional
 Materials: p-Conjugated Benzotriazinyl Radicals
;
_journal_name_full               Chem.Commun.
_journal_page_first              3201
_journal_paper_doi               10.1039/c0cc04727a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C21 H16 N3'
_chemical_formula_sum            'C21 H16 N3'
_chemical_formula_weight         310.37
_chemical_name_systematic
;

?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 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                 113.635(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.247(6)
_cell_length_b                   4.9783(11)
_cell_length_c                   26.853(6)
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.59
_cell_measurement_theta_min      2.80
_cell_volume                     3214.4(13)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_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  0.0771
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11233
_diffrn_reflns_theta_full        25.83
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0594
_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)+(0.1017P)²+0.4133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1883
_reflns_number_gt                1805
_reflns_number_total             3087
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            C0CC04727A.TXT
_cod_data_source_block           vic0710
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        3214.5(13)
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7106081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.30821(7) 0.3413(4) 0.14735(7) 0.0477(5) Uani 1 1 d D . .
N2 N 0.31184(7) 0.1519(4) 0.18526(7) 0.0453(5) Uani 1 1 d . A .
N3 N 0.40849(7) 0.2564(4) 0.23316(7) 0.0465(5) Uani 1 1 d . A .
C1 C 0.36189(9) 0.1208(4) 0.22568(8) 0.0414(5) Uani 1 1 d . . .
C2 C 0.40437(9) 0.4433(4) 0.19449(9) 0.0434(6) Uani 1 1 d . . .
C3 C 0.45130(10) 0.5939(5) 0.19906(10) 0.0514(6) Uani 1 1 d . A .
H3 H 0.4857 0.5640 0.2290 0.062 Uiso 1 1 calc R . .
C4 C 0.44822(10) 0.7833(5) 0.16096(10) 0.0557(7) Uani 1 1 d . . .
H4 H 0.4803 0.8844 0.1649 0.067 Uiso 1 1 calc R A .
C5 C 0.39806(10) 0.8289(5) 0.11626(10) 0.0543(6) Uani 1 1 d . A .
H5 H 0.3964 0.9589 0.0897 0.065 Uiso 1 1 calc R . .
C6 C 0.35097(10) 0.6854(5) 0.11057(10) 0.0515(6) Uani 1 1 d . . .
H6 H 0.3169 0.7173 0.0803 0.062 Uiso 1 1 calc R A .
C7 C 0.35373(9) 0.4936(4) 0.14941(9) 0.0445(6) Uani 1 1 d . A .
C11A C 0.2559(4) 0.347(4) 0.0995(4) 0.035(3) Uani 0.50 1 d PD A 1
C12A C 0.2108(2) 0.4377(10) 0.1102(2) 0.0449(11) Uani 0.50 1 d P A 1
H12A H 0.2153 0.4824 0.1461 0.054 Uiso 0.50 1 calc PR A 1
C13A C 0.1590(2) 0.4602(13) 0.0667(3) 0.0504(13) Uani 0.50 1 d P A 1
H13A H 0.1278 0.5226 0.0729 0.060 Uiso 0.50 1 calc PR A 1
C14A C 0.1528(6) 0.391(2) 0.0142(5) 0.053(3) Uani 0.50 1 d P A 1
H14A H 0.1173 0.3981 -0.0151 0.064 Uiso 0.50 1 calc PR A 1
C15A C 0.1988(2) 0.3138(10) 0.0054(2) 0.0590(13) Uani 0.50 1 d P A 1
H15A H 0.1948 0.2720 -0.0305 0.071 Uiso 0.50 1 calc PR A 1
C16A C 0.25068(19) 0.2953(9) 0.04773(18) 0.0493(12) Uani 0.50 1 d P A 1
H16A H 0.2823 0.2470 0.0409 0.059 Uiso 0.50 1 calc PR A 1
C11B C 0.2508(4) 0.389(4) 0.1099(5) 0.042(3) Uani 0.50 1 d PD A 2
C12B C 0.2261(2) 0.6274(11) 0.0996(2) 0.0516(12) Uani 0.50 1 d P A 2
H12B H 0.2447 0.7800 0.1200 0.062 Uiso 0.50 1 calc PR A 2
C13B C 0.1731(2) 0.6543(13) 0.0592(2) 0.0609(14) Uani 0.50 1 d P A 2
H13B H 0.1560 0.8263 0.0522 0.073 Uiso 0.50 1 calc PR A 2
C14B C 0.1456(6) 0.445(3) 0.0300(5) 0.056(3) Uani 0.50 1 d P A 2
H14B H 0.1100 0.4695 0.0015 0.067 Uiso 0.50 1 calc PR A 2
C15B C 0.1694(2) 0.1860(11) 0.0412(2) 0.0575(13) Uani 0.50 1 d P A 2
H15B H 0.1492 0.0347 0.0216 0.069 Uiso 0.50 1 calc PR A 2
C16B C 0.2226(2) 0.1546(10) 0.08142(19) 0.0500(12) Uani 0.50 1 d P A 2
H16B H 0.2398 -0.0172 0.0897 0.060 Uiso 0.50 1 calc PR A 2
C21 C 0.36492(9) -0.0853(5) 0.26678(9) 0.0449(6) Uani 1 1 d . A .
C22 C 0.41301(11) -0.1098(5) 0.31426(10) 0.0559(7) Uani 1 1 d . . .
H22 H 0.4434 0.0077 0.3199 0.067 Uiso 1 1 calc R A .
C23 C 0.41778(12) -0.3008(6) 0.35345(10) 0.0645(8) Uani 1 1 d D A .
C24 C 0.37293(14) -0.4709(6) 0.34450(11) 0.0683(8) Uani 1 1 d . . .
H24 H 0.3755 -0.6045 0.3707 0.082 Uiso 1 1 calc R A .
C25 C 0.32453(12) -0.4480(5) 0.29788(11) 0.0614(7) Uani 1 1 d . A .
H25 H 0.2939 -0.5634 0.2925 0.074 Uiso 1 1 calc R . .
C26 C 0.32070(10) -0.2571(5) 0.25906(10) 0.0519(6) Uani 1 1 d . . .
H26 H 0.2876 -0.2435 0.2269 0.062 Uiso 1 1 calc R A .
C27 C 0.46994(19) -0.3209(7) 0.40370(13) 0.1164(15) Uani 1 1 d D . .
H27A H 0.4939 -0.1722 0.4075 0.140 Uiso 0.60 1 calc PRD A 1
H27B H 0.4764 -0.4981 0.4180 0.140 Uiso 0.40 1 calc PRD A 2
C28A C 0.4891(3) -0.4747(15) 0.4400(2) 0.134(3) Uani 0.60 1 d PD A 1
H28A H 0.5243(4) -0.449(8) 0.4691(9) 0.161 Uiso 0.60 1 d PD B 1
H28B H 0.4677(14) -0.630(4) 0.4393(17) 0.161 Uiso 0.60 1 d PD C 1
C28B C 0.5048(3) -0.171(2) 0.4297(4) 0.140(4) Uiso 0.40 1 d PD A 2
H28C H 0.5365(10) -0.214(12) 0.4617(6) 0.168 Uiso 0.40 1 d PD D 2
H28D H 0.499(2) 0.007(5) 0.416(2) 0.168 Uiso 0.40 1 d PD E 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'
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
N2 N1 C7 122.90(18) . . ?
N2 N1 C11A 115.7(9) . . ?
C7 N1 C11A 120.8(9) . . ?
N2 N1 C11B 111.8(10) . . ?
C7 N1 C11B 124.8(10) . . ?
C1 N2 N1 116.02(18) . . ?
C1 N3 C2 116.10(19) . . ?
N2 C1 N3 127.2(2) . . ?
N2 C1 C21 115.2(2) . . ?
N3 C1 C21 117.57(19) . . ?
N3 C2 C3 119.9(2) . . ?
N3 C2 C7 122.1(2) . . ?
C3 C2 C7 118.0(2) . . ?
C4 C3 C2 121.0(2) . . ?
C3 C4 C5 120.4(2) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 C7 119.7(2) . . ?
C6 C7 N1 123.7(2) . . ?
C6 C7 C2 120.7(2) . . ?
N1 C7 C2 115.6(2) . . ?
C16A C11A C12A 121.5(4) . . ?
C16A C11A N1 124.7(9) . . ?
C12A C11A N1 113.6(9) . . ?
C13A C12A C11A 118.2(6) . . ?
C14A C13A C12A 120.3(7) . . ?
C15A C14A C13A 119.2(11) . . ?
C14A C15A C16A 121.4(7) . . ?
C11A C16A C15A 119.2(5) . . ?
C12B C11B C16B 121.0(4) . . ?
C12B C11B N1 124.9(13) . . ?
C16B C11B N1 114.0(12) . . ?
C11B C12B C13B 120.2(6) . . ?
C14B C13B C12B 121.5(8) . . ?
C13B C14B C15B 120.1(11) . . ?
C16B C15B C14B 119.3(7) . . ?
C15B C16B C11B 117.9(6) . . ?
C26 C21 C22 118.6(2) . . ?
C26 C21 C1 121.5(2) . . ?
C22 C21 C1 120.0(2) . . ?
C23 C22 C21 121.9(3) . . ?
C22 C23 C24 118.3(2) . . ?
C22 C23 C27 120.3(3) . . ?
C24 C23 C27 121.5(3) . . ?
C25 C24 C23 120.8(3) . . ?
C26 C25 C24 120.0(3) . . ?
C25 C26 C21 120.4(2) . . ?
C28B C27 C23 135.4(6) . . ?
C28A C27 C23 136.2(5) . . ?
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
N1 N2 1.363(2) . ?
N1 C7 1.397(3) . ?
N1 C11A 1.457(5) . ?
N1 C11B 1.457(5) . ?
N2 C1 1.336(3) . ?
N3 C1 1.340(3) . ?
N3 C2 1.366(3) . ?
C1 C21 1.486(3) . ?
C2 C3 1.405(3) . ?
C2 C7 1.416(3) . ?
C3 C4 1.370(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.394(3) . ?
C11A C16A 1.365(14) . ?
C11A C12A 1.402(12) . ?
C12A C13A 1.397(8) . ?
C13A C14A 1.396(12) . ?
C14A C15A 1.375(12) . ?
C15A C16A 1.383(7) . ?
C11B C12B 1.328(18) . ?
C11B C16B 1.427(18) . ?
C12B C13B 1.384(7) . ?
C13B C14B 1.331(14) . ?
C14B C15B 1.409(14) . ?
C15B C16B 1.391(7) . ?
C21 C26 1.389(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.386(4) . ?
C23 C24 1.391(4) . ?
C23 C27 1.491(5) . ?
C24 C25 1.385(4) . ?
C25 C26 1.384(3) . ?
C27 C28B 1.169(6) . ?
C27 C28A 1.181(5) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C1 0.9(3) . . . . ?
C11A N1 N2 C1 171.5(6) . . . . ?
C11B N1 N2 C1 -171.3(6) . . . . ?
N1 N2 C1 N3 0.6(3) . . . . ?
N1 N2 C1 C21 179.63(17) . . . . ?
C2 N3 C1 N2 -1.3(3) . . . . ?
C2 N3 C1 C21 179.63(17) . . . . ?
C1 N3 C2 C3 -179.8(2) . . . . ?
C1 N3 C2 C7 0.7(3) . . . . ?
N3 C2 C3 C4 -179.7(2) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 N1 179.3(2) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
N2 N1 C7 C6 179.0(2) . . . . ?
C11A N1 C7 C6 8.9(7) . . . . ?
C11B N1 C7 C6 -9.8(7) . . . . ?
N2 N1 C7 C2 -1.4(3) . . . . ?
C11A N1 C7 C2 -171.5(6) . . . . ?
C11B N1 C7 C2 169.8(6) . . . . ?
N3 C2 C7 C6 -179.8(2) . . . . ?
C3 C2 C7 C6 0.6(3) . . . . ?
N3 C2 C7 N1 0.5(3) . . . . ?
C3 C2 C7 N1 -179.0(2) . . . . ?
N2 N1 C11A C16A -116.5(16) . . . . ?
C7 N1 C11A C16A 54.3(19) . . . . ?
N2 N1 C11A C12A 69.2(15) . . . . ?
C7 N1 C11A C12A -120.0(12) . . . . ?
C16A C11A C12A C13A 3(2) . . . . ?
N1 C11A C12A C13A 177.8(9) . . . . ?
C11A C12A C13A C14A 0.6(15) . . . . ?
C12A C13A C14A C15A -3.1(15) . . . . ?
C13A C14A C15A C16A 1.8(14) . . . . ?
C12A C11A C16A C15A -5(2) . . . . ?
N1 C11A C16A C15A -178.5(12) . . . . ?
C14A C15A C16A C11A 2.0(14) . . . . ?
N2 N1 C11B C12B 125.6(16) . . . . ?
C7 N1 C11B C12B -46.4(17) . . . . ?
N2 N1 C11B C16B -57.9(13) . . . . ?
C7 N1 C11B C16B 130.1(12) . . . . ?
C16B C11B C12B C13B -3(2) . . . . ?
N1 C11B C12B C13B 173.4(11) . . . . ?
C11B C12B C13B C14B 0.3(14) . . . . ?
C12B C13B C14B C15B 2.5(14) . . . . ?
C13B C14B C15B C16B -2.9(14) . . . . ?
C14B C15B C16B C11B 0.5(12) . . . . ?
C12B C11B C16B C15B 2(2) . . . . ?
N1 C11B C16B C15B -174.3(9) . . . . ?
N2 C1 C21 C26 8.6(3) . . . . ?
N3 C1 C21 C26 -172.2(2) . . . . ?
N2 C1 C21 C22 -171.6(2) . . . . ?
N3 C1 C21 C22 7.6(3) . . . . ?
C26 C21 C22 C23 0.4(4) . . . . ?
C1 C21 C22 C23 -179.4(2) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C21 C22 C23 C27 179.9(2) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C27 C23 C24 C25 179.3(3) . . . . ?
C23 C24 C25 C26 1.1(4) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
C1 C21 C26 C25 179.9(2) . . . . ?
C22 C23 C27 C28B 28.8(11) . . . . ?
C24 C23 C27 C28B -151.2(9) . . . . ?
C22 C23 C27 C28A -168.8(6) . . . . ?
C24 C23 C27 C28A 11.2(8) . . . . ?
