#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:47:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180316 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/30/7153087.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_7153087
loop_
_publ_author_name
'Berezin, Andrey A.'
'Constantinides, Christos P.'
'Mirallai, Styliana I.'
'Manoli, Maria'
'Cao, Levy L.'
'Rawson, Jeremy M.'
'Koutentis, Panayiotis A.'
_publ_section_title
;
 Synthesis and properties of imidazolo-fused benzotriazinyl radicals.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6780
_journal_page_last               6795
_journal_paper_doi               10.1039/c3ob41169a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C26 H17 N4 O, 0.5(C6 H6)'
_chemical_formula_sum            'C29 H20 N4 O'
_chemical_formula_weight         440.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.813(11)
_cell_angle_beta                 90.713(13)
_cell_angle_gamma                104.161(13)
_cell_formula_units_Z            2
_cell_length_a                   7.8405(13)
_cell_length_b                   9.2163(12)
_cell_length_c                   15.484(2)
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.2780
_cell_measurement_theta_min      4.9844
_cell_volume                     1076.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6475
_diffrn_reflns_theta_full        66.99
_diffrn_reflns_theta_max         66.99
_diffrn_reflns_theta_min         4.99
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0471
_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)+(0.0775P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                2999
_reflns_number_total             3820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41169a.txt
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               7153087
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C -0.15238(19) 0.21678(18) 0.70847(11) 0.0252(3) Uani 1 1 d .
C2 C 0.0144(2) 0.33708(18) 0.60481(11) 0.0258(4) Uani 1 1 d .
C3 C 0.0886(2) 0.33182(18) 0.52341(11) 0.0261(4) Uani 1 1 d .
H3 H 0.0596 0.2443 0.4840 0.031 Uiso 1 1 calc R
C4 C 0.2074(2) 0.46130(18) 0.50275(11) 0.0253(3) Uani 1 1 d .
C5 C 0.3929(2) 0.63029(18) 0.44712(11) 0.0256(4) Uani 1 1 d .
C6 C 0.24688(19) 0.59043(18) 0.56359(11) 0.0254(3) Uani 1 1 d .
C7 C 0.1804(2) 0.60261(18) 0.64431(11) 0.0260(3) Uani 1 1 d .
H7 H 0.2119 0.6910 0.6830 0.031 Uiso 1 1 calc R
C8 C 0.0610(2) 0.47243(19) 0.66488(11) 0.0259(4) Uani 1 1 d .
C9 C 0.0208(2) 0.59137(18) 0.81238(11) 0.0263(4) Uani 1 1 d .
C10 C -0.0215(2) 0.72417(19) 0.79761(12) 0.0300(4) Uani 1 1 d .
H10 H -0.0716 0.7323 0.7442 0.036 Uiso 1 1 calc R
C11 C 0.0118(2) 0.8448(2) 0.86341(13) 0.0353(4) Uani 1 1 d .
H11 H -0.0157 0.9345 0.8541 0.042 Uiso 1 1 calc R
C12 C 0.0856(2) 0.8319(2) 0.94254(13) 0.0366(4) Uani 1 1 d .
H12 H 0.1095 0.9133 0.9863 0.044 Uiso 1 1 calc R
C13 C 0.1243(2) 0.6971(2) 0.95694(12) 0.0357(4) Uani 1 1 d .
H13 H 0.1719 0.6880 1.0108 0.043 Uiso 1 1 calc R
C14 C 0.0923(2) 0.5765(2) 0.89155(12) 0.0308(4) Uani 1 1 d .
H14 H 0.1188 0.4864 0.9010 0.037 Uiso 1 1 calc R
C15 C -0.2644(2) 0.07718(19) 0.73776(11) 0.0266(4) Uani 1 1 d .
C16 C -0.3401(2) 0.0801(2) 0.81799(12) 0.0307(4) Uani 1 1 d .
H16 H -0.3221 0.1709 0.8543 0.037 Uiso 1 1 calc R
C17 C -0.4429(2) -0.0511(2) 0.84499(12) 0.0333(4) Uani 1 1 d .
H17 H -0.4934 -0.0478 0.8990 0.040 Uiso 1 1 calc R
C18 C -0.4696(2) -0.1865(2) 0.79127(12) 0.0322(4) Uani 1 1 d .
H18 H -0.5380 -0.2745 0.8091 0.039 Uiso 1 1 calc R
C19 C -0.3944(2) -0.19082(19) 0.71116(12) 0.0312(4) Uani 1 1 d .
H19 H -0.4123 -0.2819 0.6751 0.037 Uiso 1 1 calc R
C20 C -0.2918(2) -0.05952(19) 0.68402(12) 0.0289(4) Uani 1 1 d .
H20 H -0.2417 -0.0631 0.6300 0.035 Uiso 1 1 calc R
C21 C 0.5192(2) 0.72259(18) 0.39488(11) 0.0258(4) Uani 1 1 d .
C22 C 0.6063(2) 0.87010(19) 0.42736(12) 0.0296(4) Uani 1 1 d .
H22 H 0.5831 0.9106 0.4826 0.035 Uiso 1 1 calc R
C23 C 0.7269(2) 0.9565(2) 0.37774(13) 0.0351(4) Uani 1 1 d .
H23 H 0.7836 1.0553 0.3994 0.042 Uiso 1 1 calc R
C24 C 0.7633(2) 0.8959(2) 0.29584(13) 0.0357(4) Uani 1 1 d .
H24 H 0.8445 0.9539 0.2625 0.043 Uiso 1 1 calc R
C25 C 0.6784(2) 0.7487(2) 0.26367(12) 0.0331(4) Uani 1 1 d .
H25 H 0.7042 0.7080 0.2090 0.040 Uiso 1 1 calc R
C26 C 0.5553(2) 0.66163(19) 0.31225(11) 0.0294(4) Uani 1 1 d .
H26 H 0.4973 0.5635 0.2900 0.035 Uiso 1 1 calc R
C27 C 0.4265(2) 0.5449(2) 0.07639(13) 0.0365(4) Uani 1 1 d .
H27 H 0.3776 0.5755 0.1277 0.044 Uiso 1 1 calc R
C28 C 0.3773(2) 0.3963(2) 0.03973(13) 0.0358(4) Uani 1 1 d .
H28 H 0.2949 0.3266 0.0663 0.043 Uiso 1 1 calc R
C29 C 0.4501(2) 0.3507(2) -0.03644(13) 0.0380(4) Uani 1 1 d .
H29 H 0.4168 0.2503 -0.0611 0.046 Uiso 1 1 calc R
N1 N -0.01367(17) 0.46560(15) 0.74491(9) 0.0259(3) Uani 1 1 d .
N2 N -0.11523(17) 0.33606(15) 0.77009(9) 0.0273(3) Uani 1 1 d .
N3 N -0.10075(17) 0.20989(16) 0.62705(9) 0.0267(3) Uani 1 1 d .
N4 N 0.30435(17) 0.49129(15) 0.42891(9) 0.0264(3) Uani 1 1 d .
O1 O 0.36593(14) 0.70033(13) 0.52791(7) 0.0262(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N3 C1 N2 127.73(15) . .
N3 C1 C15 118.21(15) . .
N2 C1 C15 114.06(15) . .
N3 C2 C3 119.18(15) . .
N3 C2 C8 120.66(16) . .
C3 C2 C8 120.14(15) . .
C2 C3 C4 118.25(15) . .
C2 C3 H3 120.9 . .
C4 C3 H3 120.9 . .
C6 C4 C3 119.13(15) . .
C6 C4 N4 108.81(14) . .
C3 C4 N4 132.06(16) . .
N4 C5 O1 115.43(15) . .
N4 C5 C21 129.11(16) . .
O1 C5 C21 115.45(14) . .
C7 C6 O1 126.78(15) . .
C7 C6 C4 125.54(15) . .
O1 C6 C4 107.68(14) . .
C6 C7 C8 115.21(15) . .
C6 C7 H7 122.4 . .
C8 C7 H7 122.4 . .
N1 C8 C7 122.11(15) . .
N1 C8 C2 116.13(15) . .
C7 C8 C2 121.72(16) . .
C14 C9 C10 121.17(16) . .
C14 C9 N1 119.05(15) . .
C10 C9 N1 119.76(15) . .
C9 C10 C11 119.26(17) . .
C9 C10 H10 120.4 . .
C11 C10 H10 120.4 . .
C12 C11 C10 120.07(17) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C13 120.02(17) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C14 C13 C12 120.30(17) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C9 C14 C13 119.17(17) . .
C9 C14 H14 120.4 . .
C13 C14 H14 120.4 . .
C16 C15 C20 119.06(16) . .
C16 C15 C1 121.33(15) . .
C20 C15 C1 119.60(15) . .
C15 C16 C17 120.82(16) . .
C15 C16 H16 119.6 . .
C17 C16 H16 119.6 . .
C18 C17 C16 119.82(17) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C19 C18 C17 119.85(16) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
C18 C19 C20 120.38(17) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C19 C20 C15 120.08(16) . .
C19 C20 H20 120.0 . .
C15 C20 H20 120.0 . .
C22 C21 C26 119.76(16) . .
C22 C21 C5 120.57(16) . .
C26 C21 C5 119.66(15) . .
C23 C22 C21 120.23(17) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C22 C23 C24 120.06(17) . .
C22 C23 H23 120.0 . .
C24 C23 H23 120.0 . .
C23 C24 C25 119.88(17) . .
C23 C24 H24 120.1 . .
C25 C24 H24 120.1 . .
C24 C25 C26 120.63(17) . .
C24 C25 H25 119.7 . .
C26 C25 H25 119.7 . .
C25 C26 C21 119.42(17) . .
C25 C26 H26 120.3 . .
C21 C26 H26 120.3 . .
C28 C27 C29 119.88(18) . 2_665
C28 C27 H27 120.1 . .
C29 C27 H27 120.1 2_665 .
C27 C28 C29 120.10(18) . .
C27 C28 H28 120.0 . .
C29 C28 H28 119.9 . .
C28 C29 C27 120.02(19) . 2_665
C28 C29 H29 120.0 . .
C27 C29 H29 120.0 2_665 .
N2 N1 C8 123.34(14) . .
N2 N1 C9 113.56(13) . .
C8 N1 C9 122.88(14) . .
C1 N2 N1 115.30(14) . .
C1 N3 C2 116.38(14) . .
C5 N4 C4 104.26(14) . .
C6 O1 C5 103.83(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N3 1.328(2) .
C1 N2 1.338(2) .
C1 C15 1.493(2) .
C2 N3 1.376(2) .
C2 C3 1.395(2) .
C2 C8 1.431(2) .
C3 C4 1.396(2) .
C3 H3 0.9300 .
C4 C6 1.395(2) .
C4 N4 1.398(2) .
C5 N4 1.295(2) .
C5 O1 1.381(2) .
C5 C21 1.460(2) .
C6 C7 1.363(2) .
C6 O1 1.3731(19) .
C7 C8 1.402(2) .
C7 H7 0.9300 .
C8 N1 1.379(2) .
C9 C14 1.377(3) .
C9 C10 1.387(2) .
C9 N1 1.435(2) .
C10 C11 1.387(3) .
C10 H10 0.9300 .
C11 C12 1.379(3) .
C11 H11 0.9300 .
C12 C13 1.390(3) .
C12 H12 0.9300 .
C13 C14 1.384(2) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.384(2) .
C15 C20 1.393(2) .
C16 C17 1.392(2) .
C16 H16 0.9300 .
C17 C18 1.384(3) .
C17 H17 0.9300 .
C18 C19 1.380(3) .
C18 H18 0.9300 .
C19 C20 1.393(2) .
C19 H19 0.9300 .
C20 H20 0.9300 .
C21 C22 1.394(2) .
C21 C26 1.396(2) .
C22 C23 1.383(2) .
C22 H22 0.9300 .
C23 C24 1.386(3) .
C23 H23 0.9300 .
C24 C25 1.386(3) .
C24 H24 0.9300 .
C25 C26 1.387(2) .
C25 H25 0.9300 .
C26 H26 0.9300 .
C27 C28 1.377(3) .
C27 C29 1.395(3) 2_665
C27 H27 0.9300 .
C28 C29 1.382(3) .
C28 H28 0.9300 .
C29 C27 1.395(3) 2_665
C29 H29 0.9300 .
N1 N2 1.3654(19) .
